Sunday, September 13, 2026

If you give a mouse a cookie ... (CRM progress)

I read a recent post about how Draper's investment team used to run on 8 spreadsheets but now runs on a patchwork of tools stitched together. (For example: one Airtable page per company.) I'm sure this solution functionally works well, but it's made me realize that I think like an "enterprise engineer" -- almost the complete opposite of a start-up engineer. At Epic, I've spent nearly a decade thinking about "if we add this single line of code in the wrong way..." or "if we make this data structure look like XYZ," then it's not optimal long-term. In other words, the enterprise engineer's belief is that there are many nearsighted, wrong ways to solve a problem, but only a handful of good long-term solutions. This is in stark contrast to the "move fast and break things" ethos of Silicon Valley of yore, and to the "just vibe code it" ethos of today. 

I say this in part to justify my slow movement on building my CRM tool. The tool blossomed into much more -- I'm adding in market maps along with companies (public and private), investors, etc. One thing I am spending the most time with is the data structure, or how all the different entities link to one another. To make this more concrete: yes, you can have one Airtable page per company. But then how do you link an investor to it, especially when you consider that an investor can invest multiple times in the same start-up, out of different funds? Getting this data structure right is a pain in the ass, especially if you consider that the data is sparse (if you have a cap table, you have all the info, but most of the time you just have snippets of info -- and the data structure should work for either!)

Along the way, I also realized that a good tool should allow you to centralize and share preliminary information easily, something that investment offices I don't believe do well today. For example, if I review a data room or do market research, who knows what I've searched for? (Even I forget what I found, unless I take the time to write it out!) The only way to know is to ask me, and hope that I remember or have the time (and that I remember correctly). I think this is a hidden crux of a great tool -- make organizing my knowledge easy, and thus make sharing it easy.

So this has been the "if you give a mouse a cookie" scenario for my CRM tool. It's slowly blossoming into a more all-encompassing "system of record" tool that has all the info. The other thing I've always been interested in -- and have shaped up the "marketing" of it in my head: the tool should allow you to layer public info (e.g. public articles) with private info (e.g. private phone calls, confidential pitch decks, etc.) to create a tool that can TRULY manage a mosaic of information. This requires tighter auditing and control of what data came from where -- but if successful, can be a really cool tool that mirrors how people actually think. But! the hard part is the data structure -- and knowing that the hard part is the data structure! -- something enterprise-thinking me is stuck thinking about. So, hence the continued slow roll.

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If you give a mouse a cookie ... (CRM progress)

I read a recent post about how Draper's investment team used to run on 8 spreadsheets but now runs on a patchwork of tools stitched toge...