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Failure gets talked about like it is part of the journey. That is the lie.
The real thing is messier. Missed bets. Wrong hires. Near-breakdowns. The week you stop sleeping and start doing math at 3:00 AM.
Founders are expected to eat it quietly and keep moving. No language for what happened. No playbook for what to do next.
Ugly Talk is a founder room for the part nobody posts. No fluff. No consultants. Just builders with scars, talking about the call that cost them.
Why you should be in this room.
Hear what failure cost them. Then hear what they did next.
Learn how experienced founders separate self-worth from outcomes when things go sideways.
Spot the patterns behind repeat mistakes. And the early signals you should not ignore.
Leave with a few concrete moves for the next hard week. Not inspiration.
Meet other founders in the thick of it. The ones who are still building.
What's on the table.
Dare to suck: how permission to fail unlocks real progress
The moment things broke: missed opportunities, wrong turns, near-breakdowns, and what changed afterward
Failure vs identity: separating self-worth from outcomes
Treating setbacks as data: what to measure, what to ignore, and how to decide fast
Rejection as redirection: how founders find the signal in the no
Habits for staying focused and resilient when everything feels uncertain
Run of show
6:00 6:30 PM: Reception (check-in & light drinks)
6:30 6:40 PM: Welcome remarks
6:40 6:50 PM: Keynote Speech by Ben McKean
6:50 7:30 PM: Panel Discussion
7:30 7:45 PM: Audience Q&A
7:45 8:00 PM: Mixer + snacks and drinks
Featured speakers.
Ben McKean - Founder & Chief Executive Officer, Hungryroot
Ben McKean is the Founder and CEO of Hungryroot, a personalized healthy eating assistant that uses AI to make meal planning, food shopping, and nutrition effortless and enjoyable. Prior to Hungryroot, Ben was a Vice President and General Manager at Groupon, overseeing their food and beverage business. Ben came to Groupon through the acquisition of Savored, which he founded in 2009. Savored was the nations leading provider of yield management technology to the restaurant industry, used by over two thousand restaurants nationwide and nearly one million diners. Prior to Savored, Ben worked in Merrill Lynchs technology investment banking group. Ben is a graduate of Georgetown University and currently lives in North Carolina with his wife and kids.
Stephen McKinney - Founder & CEO, Bizbe
Stephen McKinney is a serial entrepreneur with over a decade of experience across tech, marketing, and logistics. He's the founder and CEO of Bizbe.com, an AI-native business brokerage and lower middle market M&A firm based in New York and Miami. A former contestant on ABC's Shark Tank, Steve previously founded and led Retty Logistics, a seven-figure last-mile delivery company acquired by DXP Logistics and Webster Logistics.
Dmitry Koltunov - Founder and CEO, Arbor
Dmitry Koltunov is a serial entrepreneur, technologist, educator, and storyteller. He is the founder and CEO of Arbor, an AI-powered content engine that helps enterprises scale their communications with video and beyond. Previously, he co-founded and served as CTO of ALICE, a hospitality technology company that grew into a global industry leader before being acquired by Expedia Group.
Dmitry also leads the New York City chapter of the Startup Leadership Program, New Yorks oldest startup fellowship, whose 500+ alumni have collectively raised more than $1 billion in funding across every industry imaginable. He is passionate about helping founders navigate the challenges of building and scaling companies.
Outside of technology, Dmitry is an award-winning songwriter and theater producer currently developing a new musical for Broadway. He holds degrees in Computer Science and Economics from the University of Pennsylvania and is a CFA charterholder.
Gwendolyn von Rahn - Co-Founder and CEO, Sweetling Health
Gwendolyn von Rahn is the Co-Founder and CEO of Sweetling Health, an postpartum intelligence platform built for at-risk and hard-to-reach populations. Shes a second-time exited founder, an award-winning marketer with over a decade of experience building consumer brands for women, Gwen led creative and brand teams at Vogue, InStyle, and POPSUGAR before founding and scaling a mission-driven consumer brand into Nordstrom distribution that raised over $1M for melanoma research through the Melanoma Research Foundation. She holds a Cornell Johnson MBA and founded Sweetling from her own lived experience with the postpartum care gap.
Who's hosting it.
Victoria Yampolsky - President, The Startup Station
Victoria Yampolsky is the Founder and President of The Startup Station, a strategic CFO advisory firm and financial education platform for startups. She partners with founders on financial strategy, modeling, and fundraising, having supported over 150 companies across 15 industries in raising more than $50M in venture capital. Victoria is also an advocate for female founders and access to capital, and has taught finance to more than 20,000 entrepreneurs through programs including the Bank of America Institute for Womens Entrepreneurship at Cornell. She began her career at Deutsche Bank and Capgemini, and holds a BS in Computer Science from Cornell University and an MBA from Columbia Business School.
Who's getting in.
Early-stage tech founders and operators navigating uncertainty, setbacks, or the emotional weight of building a company. Expected roles may include:
Founders and co-founders (pre-seed to Series A)
Operators (COO, Head of Ops, Chief of Staff)
Product and Engineering leads building through ambiguity
Growth and GTM leads working through missed targets and pivots
Finance and strategy leaders supporting founder decision-making
Who's backing this.
The Startup Station
The Startup Station - is a CFO advisory and financial education platform for early-stage startups. We help early-stage founders build investor-ready financials and tell their funding story with confidence. In the past decade, weve helped 150+ founders raise over $50M and educated 20,000+ entrepreneurs worldwide. The Startup Station also runs Speed Pitch, an exclusive investor-founder matchmaking event series for early-stage startups where founders are matched with 3 investors by sector, stage, and check size.
Mind Your Business
Every attendee will receive a free copy of keynote speaker Ben McKeans Mind Your Business. Mind Your Business is a practical parable for people rethinking work as AI advances. Set over a four-day retreat, it follows six participants competing for funding to bring one vision to life. As they evaluate six competing proposals, they begin to confront deeper questions about what gives them energy, who they serve, and what they uniquely contribute. Those patterns form what the book calls their Soulcodethe way purpose, belonging, imagination, and courage shape how they work. Told with humor and warmth, the story turns familiar workplace tensions into practical lessons for contributing more deeply, seeing new possibilities, and acting with greater conviction. At its core, the book argues that the opportunity of the AI era isnt doing more workits knowing what work is worth doing.
GREY Journal
GREY Journal - Media partner spotlighting modern entrepreneurs (featured on Apple News + Google News).
About Ugly Talk
Started in 2019, Ugly Talk has been transforming business setbacks into breakthrough \
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