Archive - Semi-Structured

The Bull Case for Braintrust

Braintrust isn't just riding the AI wave, it enables it. We're building the critical infrastructure that will help organizations turn AI from…

Mar 6 •

So long, dbt Labs, and thanks for all the fish

About three and a half years ago, I wrote an article about my career investment thesis on dbt Labs, and now nearly four years after joining, I find…

Mar 4 •

February 2023

What to do when the 409A is changing

My company’s Slack lit up recently because of an announcement that we were going to be redoing our 409A valuation.

Feb 22, 2023 •

November 2022

The Multiples are Falling!

Hey folks, I don’t know if you’ve heard, but apparently the tech sector’s been having, like, a rough go of it lately. And if you’ve been paying any…

Nov 2, 2022 •

September 2022

What are your options when you don't have cash to exercise?

Lately, I’ve been increasingly getting asked something along the lines of: “I want to exercise my options, but I don’t have cash to do it. What options…

Sep 22, 2022 •

August 2022

How AMT impacts the startup employee

In my last article, I wrote a bit about my own personal stock exercise strategy in a down market.

Aug 24, 2022 •

June 2022

How I'm thinking about down rounds and equity during a downturn

If you’ve been under a rock lately, you might have missed that the sky is falling throughout the tech world. It’s easy to make money on stock in a bull…

Jun 28, 2022 •

March 2022

Why Instacart's new 40% lower valuation is actually fantastic for employees

Axios, among others, reported recently that Instacart had cut their valuation from $39B to $24B. In reality, lower valuations are actually a good thing…

Mar 29, 2022 •

February 2022

Is Snowflake a database?

Can you have a single database that supports all your workloads? I got asked this question the other day, and it got me thinking...The answer really…

Feb 16, 2022 •

September 2021

The reconciliation bill and the tech worker

The proposed reconciliation bill has teed up major changes to qualified small business stock and how retirement accounts work, and it could mean major…

Sep 30, 2021 •

Why early exercise matters more in today's venture funding climate

There’s pros and cons, and risks and advantages to early exercising stock options. In today’s fundraising climate, more than ever before, I believe that…

Sep 15, 2021 •

August 2021

Who's really using dbt?

dbt is data transformation technology that has become very popular with analysts, data scientists, and analytics engineers. Looking at job postings for…

Aug 18, 2021 •

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