A few days ago...
I was sweating my ass off as I walked down Kaʻahumanu when the all‑knowing YouTube algorithm served me a TechCrunch video.
GEORGe, I Can't be your apprentice, but you are still sick..
So I Listened to 12 Hours of Your Interviews, ... and Learned a Lot
Besides eating eggs with sriracha, one of my favorite things to do is understand how people think—especially the mental frameworks they rely on to succeed in their roles.
I'm particularly interested in how different people approach investing.
Here’s my reconstruction of your investing framework, based on the sources I could find online.
Generally, making investment decisions is a funneling process, sifting through all ideas to get to the flakes of gold. I.e. going from 20k ideas to ~90.
For VCs, founders sit at the top of the funnel.
What qualities do you look for in Founders?
Build a Founder
The perfect founder has:
Greed, which is an incredibly motivating factor
Desire to change the world, as they have been hurt by the way the world is
Psychological need to win, and feel important
Ability to create, demand, drive, and control attention
A product which is an extension of their personality
A rooted need to manage chaos (which usually stems from childhood tension)
Burning desire to do things that are considered impossible and prove people wrong
Grit to accomplish their vision, no matter what it takes (sleepless nights, hardcore leadership, …)
The attitude that they will achieve their vision no matter if you invest in their company or not.
Richness of thought in their domain.
Grounding in reality.
A self-made story
This isn’t to say all of these are required — just that the more boxes you check, the better.
Assuming the founder in question has passed the sniff test we proceed to the next set of questions regarding their product or service.
General Investment Questions to Answer
Does the product have high growth potential?
Does every employee have the same answer to the question “what does your company do?”
Can this company become a monopoly?
Are partners split on the decision?
Can this return a power law like multiple?
Your Specific Questions to Answer:
Does the product or service empower the individual?
Does this democratize industry x?
Would I want to join the person to pursue the project?
Do I feel more energized at the end of the meeting than the beginning?
The only thing one has in life is their intuition, in the end, listen to it.
If a product/service makes it through this funneling process, founders get ready to cash George’s check!
It is also great to learn about the daily reality of different roles.
The role of a VC is ‘simple’
- Create positive IRR (which is beneficial to LPs and the VC for the damn carry).
- Be able to meet superb founders, stand out in a hyper competitive funding landscape, and back them to change the world. If you do this long enough, you build up a pretty sweet network.
- Network with companies that can help portfolio companies.
- Recruiting.
- If you are lucky, watch friends build a successful startup!
It is nice to add another investing framework to my arsenal!
But also it was great to learn about another cool person, I'm looking at you George.
Whether it is knowing people can write better compilers in college, taking a back seat to the founder in a startup, praising mentors such as Wei Yen, Steve Blank, and Andre Radjwadowski (forgive any misspelling) , or taking 7 years to come to terms with calling yourself a good VC - I appreciate your lack of ego.
But mostly, I respect the adversity you've faced and obstacles you've overcome. Hard work, health scares, and hurricanes. Not many can come out the other side with acceptance and clarity on how to proceed in life.
Your reflection of your VPL experience resonates with me—especially your description of feeling like you’d failed after having gone broke.
At 26, all I’ve known is failure (I say this with a smile on my face).
I’m tired of my situation.
So here’s my ask...
I’m not asking for people in my corner — just a few spectators.
George, would it be okay if I send you update emails as I (hopefully) build something that moves up and to the right?
I’m not sure yet about the cadence—weekly, biweekly, maybe monthly. I don’t expect replies or feedback. I’d just like a place to send them.
I completely understand if that’s not possible — but I figured it was worth asking.
