Hosting monthly forums for founders to support each other as their companies grow.
UGLY TALK X GOOD TALK: WHAT NO ONE TELLS YOU ABOUT BEING A MIDDLE AGED FOUNDER
A small, facilitated roundtable for founders who aren't hustle-culture kids.
Bring one conversation you've been avoiding. Leave with real perspective on it, and a handful of founders who know what you're actually dealing with.
No stage. No audience. No pitching.
Facilitated by executive leadership coach Daniel Stillman, author of Good Talk: How to Design Conversations that Matter.
Who is this for?
Being a founder takes commitment, sacrifice, and sometimes hustle. But the hustle-culture narrative doesn't match the life you want as you get older. You're not 25 with nothing to lose. You have a mortgage. You want a proper vacation. Maybe you have aging parents to care for. And a mission you still want to bring into the world.
Why a Roundtable?
You don’t need another big networking event, or a poorly moderated panel you could have watched on YouTube at 2x.
You need an intimate, high-trust, off-the-record room where you can get real with other founders, builders and entrepreneurs.
A roundtable is one where everyone shares, everyone is heard, and everyone gets more than they imagined.
The Conversation
Conversations are the atomic unit of change. Our lives are built by the conversations we have, and defined by the ones we avoid. The cofounder conflict you brush off but never resolve. The hire you won't admit isn't working. The pivot you keep putting off.
The ones we avoid most are with ourselves. The bargains we never renegotiated. The anxiety we can't politely ask to leave. The question we keep not answering.
The un-had conversation doesn't disappear. It goes underground and gets more expensive. This roundtable is designed to create the space for the most important questions and conversations you’re facing right now.
Application and Curation
Admission is by application - please complete all application questions so we can curate the group, optimizing for:
People actively building
Openness, Curiosity and Generosity
Commitment - people who don’t show up won’t be invited to come again
The Prework:
This is a small room, on purpose, so we’re only selecting a handful of folks who are willing to do some thinking before they get in the room. Apply with your thoughtful answers to the registration questions.
The Format:
Five rounds of conversation:
Connection and Learning - so we know who we are and why we’re building what we are each building
Exploration: Sharing your avoided conversation with the group - what's a conflict or tension you're sitting with?
Stories Vs Advice: Sharing stories to help each other through shared empathy, not problem solving
Asks and Offers: What’s something you need from the group? What’s something you can offer in generosity?
Closing Round - What you’re taking away from the conversation - what you’re committed to
The Follow Up:
Join a continuing conversation with the attendees, where you can share the resource you mentioned, ask that follow-up question, and get the support you need from a generous, growing community.
Your Co-Hosts
Daniel Stillman designs conversations for a living, and insists that you do too. He's an executive coach and facilitator who works with founders and founding teams on how they lead, communicate, and navigate the conversations that matter. He hosts The Conversation Factory podcast (a top 100 Management podcast) and wrote Good Talk: How to Design Conversations that Matter, a handbook for changemakers and innovators.
Anson Wu is the founder of Ugly Talk, the no-BS event series where battle-tested founders share the setbacks, pivots, and lessons behind the wins. Since 2019 it's grown across New York, Chicago, San Francisco, and Miami. Anson also runs Grey Journal, the digital media company behind it, and came up as a designer and agency founder. By his own description, a recovering underthinker still mining the lessons from two failed startups.
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
Hosting monthly forums for founders to support each other as their companies grow.