It was 6:45 AM on a fall Tuesday morning, and I was sitting at Burbank Airport waiting for my routine flight to Oakland. My calendar was packed: back-to-back meetings chasing Bay Area AI deals, portfolio company fire drills, and figuring out the week’s family logistics—like where to take the boys trick-or-treating.

As I blasted through my backlog of emails—deleting most—I came across one that stopped me in my tracks:

Subject Line: 1Up Seed

Hi Kobie, it's George @ 1Up. We're seeing 500% QoQ growth and I'm putting together a seed round. 1Up automates knowledge for sales teams ($22B TAM). Sales teams use 1Up to answer customer questions, automate RFPs, and complete compliance questionnaires 10x faster. Our customers from across the globe include SMBs like Gladly and enterprises like WalkMe SAP.

Who would be the right partner to connect with on your team?

My initial reaction: 🙋🏽‍♂️

I immediately emailed George back, thanked him for the note, and asked how much he was raising.

Two minutes later, George replied: “$2-4M priced round. You’re on my list, and I just started the process.” He mentioned a few of his prior investors—funds we know well.

Boom. It checked several boxes:

• A clear articulation of the problem.
• Alignment with a thesis I was already exploring.
• Validation through credible prior investors.

I replied, asking him to schedule a meeting. George shot over a Calendly link, and I grabbed time two days later, bypassing my usual process of working through Nancy, my EA.

In 20 minutes, the initial qualification stage was done, and I had a gut feeling: there’s something here.

Meeting George: The Light Saber Moment

Two days later, George and I connected over Zoom. One of the first things he said was, “Is that a light saber behind you?”

I froze. I have a bunch of toys behind my desk and was preparing to get roasted for being the uber nerd I am. Sheepishly, I said, “Yes.”

Without missing a beat, George reached off-screen, grabbed his own light saber, and held it up to the camera. In true Jedi fashion, he made it clear: this wasn’t your average pitch meeting.

In that moment, I knew George wasn’t just another founder. He had the perfect mix of technical expertise, creative energy, and mission-driven ambition that we look for. That light saber wasn’t just a prop—it was a metaphor for the shared excitement we had about tackling an enormous opportunity together.

Why This Email Cut Through the Noise

The question you may be asking is: why did George’s email stand out and what got me so excited to work with George?

It wasn’t the 500% quarter-over-quarter growth stat (although that didn’t hurt). What grabbed my attention was the clear articulation of a problem and how 1Up was solving it—perfectly aligned with a thesis I had been developing around knowledge systems and the opportunity to transform sales processes. Additionally, George and I were able to instantly connect as human beings in our first zoom. Not only was this a case of meeting a founder tackling an exciting market opportunity, it was one of also meeting another individual you are truly excited to partner with.

The Problem 1Up is Solving

When I was CMO at REVOLVE the vendors I loved working with most were the ones who could immediately address my technical concerns and move the process forward. Whether it was delivering quick, accurate RFP responses or answering integration questions on the fly, these teams stood out because they were knowledgeable and able to keep up with me - the buyer.

When I read George’s initial email, I immediately saw how 1Up could transform enterprise sales by solving these exact pain points. 1Up automates knowledge management for sales teams, allowing reps to retrieve technical information, answer customer questions, and complete RFPs in real time. This is done through a variety of ways:

1. Automate RFP Responses:

• Retrieve data from documentation and past responses.
• Use AI to generate polished answers in minutes.

2. Provide Instant Answers:

• Act as a virtual SE, delivering accurate, contextually relevant responses on the spot.

3. Empower Sales Reps:

• Bridge the knowledge gap between sales reps and SEs, boosting confidence and effectiveness.

1Up fits into a broader thesis we have around the power of knowledge systems in enterprise software. Knowledge systems, as we see them, are platforms that unify structured and unstructured data, apply intelligence to contextualize it leveraging the power of retrieval-augmented generation (RAG), and enable users to take action. In the case of 1Up, this action is singularly focused: helping sales teams close deals.

If there’s one takeaway from this story, it’s this: even a cold email can cut through the noise when it hits the right thesis. George’s email did exactly that, and we couldn’t be more excited about what we’ll accomplish together.