If you haven’t been keeping up with the news, Biden’s infrastructure bill has been slowly progressing (or not) through the legislative system. The contents of the actual infrastructure bill is pretty well understood at this point, but Congress is using reconciliation to split apart the spending portion from the “how…


If your company allows early exercise, it makes things really interesting as an employee with a chunk of options. The effect is that you can make the decision as early as day 1 (well, really, whenever your option grant is approved) of your employment to exercise your options and get…


And is Analytics Engineering really that different from Data Engineering?

If you’re not yet familiar with dbt, it’s a data transformation technology that is widely used to enable ELT workflows in the modern data stack (which these days generally means: an ingest tool like Fivetran or HVR, a transformation tool…


After I posted an article about Peter Thiel’s $5B Roth IRA a couple weeks ago, I had a handful of readers reach out to me asking if this was something that early employees could also do. It’s an interesting question, for sure: if this can be such a huge tax…


Data has been the common theme throughout my career. I’ve spent the vast majority of the past decade working for various data infrastructure vendors, and data has always been core to my personal thesis on where I wanted to spend my career, and invest my dollars in the private markets…


My wife and I are avid readers of Matt Levine’s Money Stuff newsletter (if you’re not subscribed to that, and you generally like the things that I put out, it’s definitely worth a look). The other day, they had a section discussing a recent ProPublica (which has been on a…


I’ve been working on building out a right-sized emergency fund over the last couple years, and one of the questions I find myself constantly trying to optimize around is: where do I park my cash to get the best interest rates? My general goal with holding onto a long-term emergency…


There are a lot of rapid-fire, huge funding rounds happening right now. Capital is flowing at historically low prices, huge rounds are happening faster than ever, with more competition than ever, and cleaner terms than ever. This is great for companies and tenured employees, but can be perilous for new…


Read this story in full for free at my Semi-Structured Substack

So, uh…anybody noticed how companies seem to be raising money way faster these days? I’ll admit, I haven’t actually looked at the raw data to confirm this (mostly because I’m too lazy to try to pull that data from…


I was having a discussion with a friend recently, who was inquiring about some of my philosophies on open-source and asked: “when does open-source make sense for a business?” …

Natty (Jon Natkins)

Product guy interested in security, data infra, analytics, and finance. Currently at Fishtown, ex-Cloudera/Vertica/StreamSets. My thoughts are semi-structured.

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