UGLY TALK: THE MISTAKE THAT ALMOST ENDED IT

Most companies do not die in one dramatic moment.

It starts with a call that looked right at the time. A sales plan that burned cash. A cofounder fight nobody addressed. A funding round that disappeared. An operational miss that put the whole company at risk.

This Ugly Talk goes straight into those moments.

• The warning signs founders saw too late.
• The hard calls they made with incomplete information.
• The moves that bought them time, trust, or another shot.
• The ways a major setback changed how they hired, raised, sold, and led.
• Proof that one ugly decision does not have to be the last one.

• The mistake: What decision set the problem in motion?
• The moment it got real: When did you know the company was in danger?
• The cost: What did the mistake take from the business, the team, or you?
• The hard call: What did you choose when every option carried a consequence?
• The move: What bought the company another chance?
• The scar: What do you see now that you could not see then?

Deveney Williams - Founder & CEO, Sunny Side Up

Deveney Williams is the founder and CEO of Sunny Side Up, an embedded creative agency for growth-stage B2B SaaS founders. With 10+ years across brand strategy, creative operations, and visual storytelling for brands like Adobe, NPR, and Liberty Mutual, she now partners with founders to turn traction into a brand the market actually remembers. Curiosity is her operating principle, and clarity is the deliverable. Based in Boston, she splits her time between client work, building SSU’s team, and finding the city’s best cortado.

• Founders carrying a decision they cannot afford to get wrong.
• Cofounders working through friction before it becomes a fracture.
• Early-stage operators making big calls with limited time and cash.
• Investors and leaders who stand beside founders when the story gets ugly.

Venture Lane

Venture Lane serves early-stage B2B tech founders who seek acceleration and meaningful connection. We provide a curated startup hub that brings together human connection and focused programming to help founders make real progress across capital, customer, talent, and product milestones.

Sunny Side Up

We’re the embedded creative team for B2B SaaS founders who’d rather build than babysit creative work.

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

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• Report any violations to the event hosts immediately.

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Venture Lane, 55 Court St. Floor 2, Boston, United States

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