UGLY TALK: FAILURE IS KEY TO SUCCESS

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 Attend

• 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.

🙋 Who's Getting In This Room

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 Taking the Stage

Dmitry Koltunov - Founder and CEO of 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 York’s 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.

Stephen McKinney - Founder & CEO ofBizbe

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.

Gwendolyn von Rahn - Co-Founder and CEO of 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. She’s 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.

Moderator:

Victoria Yampolsky - President at 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 Women’s Entrepreneurship at Cornell. Victoria also runs premiere Speed Pitch events connecting founders and investors in 1:1 meetings. 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.

💬 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: Networking

• 6:30 – 7:15 PM: Panel Discussion

• 7:15 – 8:00 PM: Networking

​🎁 Additional Perks

As part of our commitment to supporting founders, The Startup Station is offering all attendees four bonuses valued at $150.

• Essential Fundraising Pack ($50 value)

  • 50 Most Frequently Asked Investor Questions (including financial questions)

  • Sample intro letter template for investor outreach

  • Business Model Analysis Roadmap - A Guide to Creating Credible Financial Model Assumptions

• *“Nail Your Financial Pitch” $100 value) - Recording of the 60-Min Master Class and Presentation

🤝 Who's Hosting It

The Startup Station is a CFO advisory and financial education platform for early-stage startups. We help founders build investor-ready financials and tell their funding story with confidence. Over the past decade, we’ve supported 150+ founders in raising over $50M and educated 20,000+ entrepreneurs worldwide. The Startup Station also runs Speed Pitch, an investor-founder matchmaking series where startups are matched with investors based on sector, stage, and check size.

🤝 Who's Backing This

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 “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

📢 ​Important Notice for Ugly Talk Attendees

Admission & Confirmation
Attendance is by approval only. Approved guests will receive a confirmation email along with a calendar invite. Invitations are non-transferable. Additional event details will be shared as the event approaches.

Code of Conduct
By attending, you agree to:

• Maintain respect and professionalism, adhering to all venue rules, policies, and applicable laws.

• Refrain from harassment, discrimination, unwelcome sexual advances (verbal or physical), intimidation, or inappropriate photography/recording.

• Report any violations to the event hosts immediately.

Violations may result in immediate removal from the event and exclusion from future invitations.

Liability & Risk
Participation is voluntary and at your own risk. The event organizers, hosts, sponsors, and venue are not liable for personal injury, lost or stolen belongings, or any other damages incurred during the event.

Media Consent
By attending, you grant the event organizers and affiliated entities the right to capture, use, and distribute photos, videos, and audio recordings of you for promotional, marketing, and other lawful purposes, including digital and print media, advertising, and social media. You waive any right to inspect or approve the final materials and release all claims related to their use.

Communications
By registering, you agree to receive marketing and promotional communications from Ugly Talk and its co-hosts, partners, and sponsors. You may unsubscribe at any time.

Agreement
If you do not agree to this Code of Conduct, please refrain from attending the event.

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