Ugly Talk cover art

Ugly Talk

Ugly Talk

Written by: Ugly Talk
Listen for free

About this listen

A Podcast About the UGLY Side of the Entrepreneurial Journey.

Anson Wu & Matthew Jaffe get into conversations with entrepreneurs, who are eager to share their stories, the good ones, the bad ones and especially the ugly ones.

Our podcast resonates with entrepreneurs at all stages of their journey, from aspiring dreamers to established founders. It serves as a voice of shared struggles and triumphs, reminding listeners that entrepreneurial life can be a journey of failure, resilience, and success.

Want to get on the show and share your Ugly stories? Go to uglytalk.com/podcast and send us a message!

2024 PodTechs
Economics Leadership Management & Leadership
Episodes
  • UGLY TALK: FOOD & BEV FOUNDERS 2025 LESSONS AND 2026 PREDICTIONS
    Feb 11 2026

    Recorded live at The Yard in Herald Square, this edition of Ugly Talk dives into the unpolished reality of building and scaling a food and beverage brand in 2025. This isn't about the highlights—it's about the messy formulation tweaks, the grind of "pounding the pavement" in New York City, and the hard-earned lessons that come with trying to move product off a retail shelf.

    Moderated by Glenn Johnson (Marketing Consultant & Fractional CMO), the panel brings together three founders building their brands in real time:

    • Joe Rotondo (Founder & CEO, SMEARCASE) shares the journey of turning cottage cheese ice cream into a high-protein sensation, detailing how a chance outreach from Whole Foods turned into a tri-state launch.
    • Kabir Kurani (Founder & CEO, GetUp Nutrition) discusses the "ugly" side of manufacturing overseas and the sheer hustle required to sell through a nationwide trial at 455 Sprouts locations.
    • Will Custis (Founder, HoopFuel) breaks down the "Corporate Hooper" persona and his hyper-focused strategy of dominating the basketball category through community events and equity-based creator partnerships.

    You’ll hear their unfiltered takes on:

    • The Power of Niching Down: Why speaking to everyone means speaking to no one, and how to identify your "hyper-focused lens".
    • The "Ugly" Side of R&D: Handling flavor failures, bitter caffeine maskings, and shipping 50 pounds of dry ice across Brooklyn.
    • Retail Reality vs. Hype: The difference between getting on the shelf and actually hitting the velocity targets required to stay there.
    • Community as a Growth Engine: Hosting tournaments and "demoing" in unmarked containers to get unbiased feedback from the right audience.
    • 2026 Strategy: How to move from a "pounding the pavement" founder to a scalable business with smart creator ecosystems and regional dominance.

    Chapters

    00:00 – Intro: The importance of niching down and hyper-focus.

    01:00 – Housekeeping: Ugly Talk’s national footprint and host introductions.

    02:00 – Sponsor Spotlight: AI-powered operations with Copley.

    04:20 – Meet the Founders: Elevator pitches for Smearcase, GetUp, and HoopFuel.

    07:13 – The "Corporate Hooper": Building a brand through a social persona.

    08:50 – Validation: Testing cottage cheese ice cream in marathon training groups.

    10:56 – Finding the Gap: Why basketball players were ignored by traditional nutrition.

    14:40 – The Co-Founder Fit: Balancing brand vision with strategy and ops.

    16:00 – Creative Expression: Why every entrepreneur should start a clothing brand.

    20:50 – Scientific Formulation: Using sweat-tracking patches to design HoopFuel.

    23:20 – The Bias Trap: Getting honest feedback outside of friends and family.

    26:00 – The Failed Batch: Selling through "disgusting" product to fund the fix.

    28:50 – The Super Bowl Moment: Landing Whole Foods via a "janky" website.

    34:15 – The New Influencer Model: Moving from one-off posts to equity-based creators.

    40:55 – The Network Effect: Using Manhattan dominance to fuel word-of-mouth.

    44:30 – Advice to Self: The logistical nightmare of dry ice and being "supply ready".

    Want to share your Ugly story? Visit uglytalk.com/podcast and send us a message.

    Show More Show Less
    47 mins
  • Ugly Talk Live: Leveraging AI to Optimize Ecommerce Logistics and Profits
    Jan 14 2026

    Recorded live, this edition of Ugly Talk dives into the real, unpolished side of scaling ecommerce operations with AI — the messy systems, the tool overload, the margin pressure, and the hard tradeoffs that come with growing fast.

    Moderated by Manish Chowdhary (Founder & CEO, Cahoot), the panel brings together operators and investors who work at the intersection of logistics, technology, and growth:

    Brian O’Connor (CEO, Aevisor Solutions) breaks down how founders can turn operations into a self-funding growth engine by freeing up cash, improving margins, and building systems that scale.

    Mat Kaliski (Principal, Acronym Venture Capital) shares how investors evaluate operational discipline, AI adoption, and resilience when backing early-stage ecommerce and technology companies.

    Frank Pacheco (Amazon Guru, Nearly Natural) delivers hard-earned lessons from inside Amazon and beyond, revealing how the best brands use AI, data, and logistics strategy to win where “best practices” fall short.

    You’ll hear their unfiltered takes on:

    • The highest-leverage improvements brands can make in the next 7 and 30 days
    • Common scaling mistakes teams repeat — and how to avoid them
    • Choosing the right tools without creating costly tech sprawl
    • Practical AI workflows for order management, support, merchandising, and reporting
    • Simple scorecards to measure speed, accuracy, and cost
    • Hiring and vendor decisions that keep operations lean and resilient

    If you’re an ecommerce founder, operator, or leader trying to protect margins while scaling smarter, this conversation cuts through the hype and gets into what actually moves the needle.

    Want to share your Ugly story?

    Visit uglytalk.com/podcast and send us a message.

    Show More Show Less
    1 hr and 8 mins
  • Ugly Talk Live: Building Effective Personal Brand for Founders.
    Dec 3 2025

    Recorded live, this edition of Ugly Talk dives into the real, unpolished side of building a personal brand as a founder — the cringe, the doubts, the consistency, and the unexpected wins that come from simply showing up online.

    Moderated by Ben Buaron (Founder & CEO, Windmill Growth), the panel brings together two operators who’ve turned content into a growth engine:

    Ben Sharf (Co-Founder & Co-CEO, Platter) shares how LinkedIn became his top acquisition channel — driving clients, hires, and even a six-figure inbound investment.

    Blaine Davis (Co-Founder, Superconnector; GP at Mute Ventures) breaks down how personal brand powers trust, warm intros, and early-stage momentum — even while staying in stealth.

    You’ll hear their unfiltered takes on:

    • Overcoming the fear of cringe and publishing anyway
    • What authenticity actually looks like online
    • How founders convert content into revenue, pipeline, and investor interest
    • Balancing top-, mid-, and bottom-of-funnel content
    • Why personal brand is becoming non-negotiable in 2025

    If you’ve ever wondered whether posting is “worth it,” this conversation pulls back the curtain on how founders really build leverage through content.

    Want to share your Ugly story?

    Visit uglytalk.com/podcast and send us a message.

    Show More Show Less
    33 mins
No reviews yet