UGLY TALK: CONNECTING, COMMUNICATING AND COLLABORATING WITH NEW AUDIENCES
Connecting with new audiences isn’t harder because there are fewer options. It’s harder because there are too many.
Business owners and professionals are juggling in-person events, digital platforms, social media, AI tools, and partnership opportunities, often without clarity on what actually drives connection, trust, or growth. Activity feels productive, but impact is inconsistent. Messages get diluted. Relationships stay shallow.
This Ugly Talk focuses on how connection, communication, and collaboration are really evolving and how to reach new audiences with intention, clarity, and credibility in a crowded, fast-changing landscape.
🎯 Why You Should Attend
Learn from real wins and missteps. Hear how operators and business owners tested different ways to connect, communicate, and collaborate and what actually moved the needle.
Get practical approaches you can use now. Concrete tactics across in-person, digital, and partnership-driven outreach, including what’s worth testing and what’s not.
Gain clarity on where to focus. Understand which channels, messages, and tools (including AI) effectively reach new audiences and where they dilute impact.
Set realistic goals for connection and trust. Learn how to measure resonance, engagement, and relationship-building so you know when to double down or pivot.
🙋 Who You’ll Meet
Small business owners and professionals focused on audience growth
Founders and operators responsible for marketing, outreach, or business development
Community builders and relationship-driven leaders
Advisors and collaborators navigating modern engagement strategies
🎤 Who’s on the Panel
DeRondal Bevly - Founder & Managing Director at RubyRose Strategies
DeRondal Bevly is the Founder and Managing Director of RubyRose Strategies, where he advises executives, founders, and civic leaders on narrative power, attention strategy, and decision-making in moments of volatility. With nearly two decades of experience across public affairs, media, and leadership development, his work sits at the intersection of culture, systems, and influence. DeRondal is also an adjunct professor in business and entrepreneurship, a leadership coach, and a frequent facilitator for senior cohorts and boards. His work blends systems thinking, cultural insight, and practical execution to help leaders move from clarity to action.
Scott Baskin - CEO of SBAC
Scott Baskin is the current CEO of the Small Business Advocacy Council. Scott retired as President and CEO of Mark Shale. Mark Shale was Chicago’s largest independent clothing retailer with stores in Chicago, Atlanta, Dallas, Kansas City, and St. Louis. Prior to his business career, Scott served as Chief Legislative Assistant to the late Congressman Abner Mikva. In addition to his professional experience, Scott is an engaged community leader. He is a board member of Uptown United, an economic development organization serving Chicago’s Uptown neighborhood. He was an elected member of the Northside College Prep High School Local Council and chair of its finance committee, past treasurer of the Center for Law and Social Work and past board member of WBEZ, Chicago Public Media. He advises and mentors several Chicago based small and medium size businesses. He is a graduate of Vassar College and Northwestern University School of Law.
Karen Kimsey-Sward - COO at Dale Carnegie Chicago
Karen Kimsey Sward is a seasoned executive with over 30 years of experience helping organizations elevate performance, strengthen leadership, and build engaged, high performing cultures. As COO of Dale Carnegie Chicago, she cultivates an engaged internal team while partnering with clients to strengthen leadership, culture, and the people capabilities that fuel long term success. Her background includes serving as VP of Franchising for the Americas at Dale Carnegie & Associates, co-founding a management consulting firm, and acting as EVP/COO of a leading sales training company. A published writer, accomplished speaker, and certified executive coach, Karen focuses on emotional intelligence, leadership effectiveness, and sustainable performance. She also serves on several boards, including the SBAC.
Moderator:
Elliot Richardson - President and Co-Founder of SBAC
Elliot Richardson is the Co-Founder and President of the Small Business Advocacy Council. The SBAC advocates for the small business community, providing a unified and strong voice on issues that impact small businesses, local communities, and the economy. The SBAC brings small businesses together to form meaningful connections for those involved.
💬 What We’ll Talk About
How connection and collaboration are changing
What’s different today and how to stay ahead as expectations evolve.
In-person vs. virtual engagement
When face-to-face still matters, when digital works better, and how to use both intentionally.
Communicating in a tech-driven world
How AI, social platforms, and new tools are reshaping audience engagement.
Using AI without losing trust
Where AI supports clarity and scale, and where human judgment still matters most.
Collaboration as a growth strategy
How strategic partnerships expand reach, credibility, and access to new audiences.
Finding focus amid endless options
How to choose the right channels and know when it’s time to pivot.
Message resonance and trust-building
How to assess what’s landing, refine your message, and build lasting relationships.
🤝 Co-hosted With
SBAC supports the small business community through nonpartisan, policy-driven advocacy and by fostering connectivity and collaboration through engagement and events.
🤝 Supported By
GREY Journal – Media partner spotlighting modern entrepreneurs (featured on Apple News + Google News).
🤝 Venue Partner
The Yard - Private offices & coworking spaces for individuals and teams.
⭐ 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.
Official Website: UglyTalk.com
📢 Important Notice for Ugly Talk Attendees
Admission & Confirmation
Attendance is by approval only. Approved guests will receive a confirmation email along with a calendar invite. Invitations are non-transferable. Additional event details will be shared as the event approaches.
Code of Conduct
By attending, you agree to:
Maintain respect and professionalism, adhering to all venue rules, policies, and applicable laws.
Refrain from harassment, discrimination, unwelcome sexual advances (verbal or physical), intimidation, or inappropriate photography/recording.
Report any violations to the event hosts immediately.
Violations may result in immediate removal from the event and exclusion from future invitations.
Liability & Risk
Participation is voluntary and at your own risk. The event organizers, hosts, sponsors, and venue are not liable for personal injury, lost or stolen belongings, or any other damages incurred during the event.
Media Consent
By attending, you grant the event organizers and affiliated entities the right to capture, use, and distribute photos, videos, and audio recordings of you for promotional, marketing, and other lawful purposes, including digital and print media, advertising, and social media. You waive any right to inspect or approve the final materials and release all claims related to their use.
Communications
By registering, you agree to receive marketing and promotional communications from Ugly Talk and its co-hosts, partners, and sponsors. You may unsubscribe at any time.
Agreement
If you do not agree to this Code of Conduct, please refrain from attending the event.
Official Event Page: [Link]