The first honest room most founders ever walk into. An invite-only IRL event series where builders talk about the part that didn't make the press release. The hard calls. The real pivots. The moments they almost quit.
Ugly Talk Website Video Jun 16 2025 (1).mp4
We bring founders together to talk about what actually happened. Not the highlight reel. The real decisions, the tradeoffs that cost something, and what they would do differently.
Ugly Talk has two high-impact segments.
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This is where founders say the quiet parts out loud. You hear the real decisions, the real costs, and walk away with moves you can make the next morning.
Meet the founders who built it the hard way.
These are real operators with scars, not polished talking heads. They share specific wins, specific misses, and takeaways you can apply today.
Field-tested insights with real numbers.
You will hear what worked, what failed, and what the data actually said. You will leave with playbooks to study and landmines to avoid.
Ask, challenge, and get answers.
Your questions drive the conversation. You can press for clarity in the moment and get practical input tailored to your situation. You will also hear questions from others who are wrestling with the same problems.
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This is where the real conversations happen. You compare notes, challenge assumptions, and meet people who are grinding through the same problems you are.
Meet founders in the same fight.
Connect with peers who are building right now. Not networking for sport. Building for real.
Ask the questions you can't ask anywhere else.
Find out where others hit walls, what they did about it, and what they wish someone had told them sooner.
Find the people who make you sharper.
Meet operators who get it. The kind who send you a useful intro the next day, not a "let's circle back" email.
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Ugly Talk: Marketing Leadership in West Loop Chicago
Ugly Talks come in three formats. Each one is built for a different level of reach and audience engagement.
Community-organized and intentionally intimate.
City-based Ugly Talk with strong local energy and built-in distribution.
Mute UT Ecomm Shopify May 2025.mp4
Region-scale Ugly Talk with the biggest reach and the biggest names.
Ugly Talk started in Chicago in 2020. Now it runs in 6 cities, with more launching soon.
From Fortune 100 companies to fast-scaling startups, these brands show up because the founders in the room are the real deal.
Last updated March 6, 2026