The AI Operator’s Playbook: How to Scale Your Team and Secure Funding

Name: The AI Operator’s Playbook: How to Scale Your Team and Secure Funding
Start: 2025-12-09T18:00:00-05:00
End: 2025-12-09T21:00:00-05:00
Location: The Yard: Herald Square

Dec 9, 2025, 11:00 PM – Dec 10, 2025, 2:00 AM (UTC)

New York City

The Yard: Herald Square, 106 West 32nd Street, New York, 10001

Talent is destiny. Richard Hughes at Gutter Capital isn't just an investor. He builds teams, recruiting 100+ hires for his portfolio. On Dec 9, we dismantle his operator's playbook for hiring better and keeping talent longer. Plus: get the inside track on Elbow Grease, their new $300k AI accelerator.

In-person event

About this event

Most early-stage founders treat hiring as a fire drill, especially in the AI era. They hire fast in order to fill gaps, only to face culture cracks and churn six months later.
Richard Hughes doesn't work that way. 🙅
As Operating Partner at Gutter Capital, he rolls up his sleeves and recruits directly alongside his portfolio companies. As a result, Gutter portcos see more than 80% employee retention at 18 months (significantly higher than the industry average).
On December 9th, we’re sitting down with Richard to dismantle the standard startup recruiting playbook. We’ll cover his philosophy on hiring fewer people, hiring them better, and keeping them longer.
WHAT YOU'LL LEARN
Cross-Functional Evaluation: How to assess and validate candidates in areas outside your own expertise (e.g., a non-technical founder hiring their first AI engineer).
The Closing Framework: A structured approach for decision-making during late-stage negotiations to secure top prospects without losing leverage.
Lo-Fi Talent Magnets: Scrappy, low-cost methods to position your company as a destination for top-tier talent, even before you have the brand recognition.
The "Curve of Excellence": How to structure an interview process that builds conviction over time rather than just checking functional boxes.
Special Focus: The Elbow Grease Accelerator. Richard is also spearheading Gutter's new AI accelerator, Elbow Grease, which offers $300k in funding and runs locally in NYC. 
If you are building in AI and looking for more than just cash, you need to be in the room to hear what they are looking for as they start recruiting for cohort #2.
WHO SHOULD ATTEND
Pre-seed/Seed founders building their founding teams.
Operators looking to transition into high-growth startup roles.
AI builders interested in the Elbow Grease accelerator program.
Tickets for this event include food and drinks, as well as exclusive access to this VC who will change the way you're building teams.
You'll also meet dozens of other high-performing entrepreneurs who are creating their next big thing. Seriously, it's some of the best founder networking in the city.
Getting a ticket guarantees admission. No waitlisting.
AGENDA
6:00 PM: Networking, Food & Drinks
7:00 PM: Fireside Chat with Richard Hughes
8:00 PM: Meet the Speaker
And don't miss our other monthly tech events. They are great opportunities for builders, founders, and operators to network with each other to share best practices and find new resources to grow your startup the right way. See our full event lineup here.