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Seen Enough to Know the Risks. Crazy Enough to Take Them.
A small roundtable for founders who grew out of hustle culture & kept building anyway.
Bring one conversation you've been avoiding. Leave with a clearer view of it, & a handful of founders who know what you're dealing with.
No stage. No audience. No pitching. Nothing said here leaves the room.
Facilitated by executive coach Daniel Stillman, author of Good Talk: How to Design Conversations that Matter.
Who is this for?
You're not 25 with nothing to lose. You have a mortgage. You'd like a real vacation this year. Maybe your parents need more of you than they used to. And you still have something you want to build.
The hustle story doesn't fit that life. The ambition didn't go anywhere.
Why a Roundtable?
You've been to the big mixer. You've sat through the panel you could have watched on YouTube at 2x.
This is a small, off-the-record table where every person talks & every person gets heard. Founders get honest faster when there's no one to perform for.
The Conversation
Our lives are built by the conversations we have, & defined by the ones we avoid.
The cofounder conflict you brush off every week. The hire you won't admit isn't working. The pivot that's been "next quarter" for 3 quarters. The runway number you haven't said out loud.
The hardest ones are with yourself. The bargain you made years ago & never renegotiated. The anxiety you can't politely ask to leave.
An avoided conversation doesn't disappear. It goes underground & gets more expensive.
Bring one.
How to get a seat
Admission is by application, & the questions are the prework. Give them real answers. That's how we build the table.
We pick people who are building right now & who care about the other founders' problems as much as their own. One house rule: if you're accepted & don't show, you won't be invited back.
The Format
5 rounds, in order:
Who's here. Who you are & why you're building what you're building.
The avoided conversation. Each person puts theirs on the table: the conflict or tension they're sitting with.
Stories over advice. The group answers with what happened to them. Nobody tries to fix you.
Asks & offers. One thing you need from the group. One thing you can give.
Close. What you're taking with you, & what you'll do about it.
The Follow Up:
You'll join an ongoing thread with the people at your table. Send the resource you promised. Ask the follow-up you thought of on the train home.
Your Co-Hosts
Daniel Stillman designs conversations for a living, & insists that you do too. He's an executive coach & facilitator who works with founders & founding teams on how they lead, communicate, & navigate the conversations that matter. He hosts The Conversation Factory podcast (a top 100 Management podcast) & wrote Good Talk: How to Design Conversations that Matter, a handbook for changemakers & innovators.
Anson Wu is the founder of Ugly Talk, the no-BS event series where battle-tested founders share the setbacks, pivots, & lessons behind the wins. Since 2019 it's grown across New York, Chicago, San Francisco, & Miami. Anson also runs Grey Journal, the digital media company behind it, & came up as a designer & 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 & insights.
With a growing presence in cities like New York, Chicago, San Francisco, & Miami, we've built a vibrant community of thousands of founders & industry leaders making a profound impact on the entrepreneurial landscape.
Official Website: UglyTalk.com
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