Aaron's Essays
1, 7, 30, 11, 12
Jews do mourning well. That’s what I’ve always thought from watching family and friends go through...
4th Feb 2026
Jews do mourning well. That’s what I’ve always thought from watching family and friends go through it. It’s what I’ve learned as fact since my father died eleven months ago.
There’s a central tension to it. A constant fault line that our customs straddle. It’s the constant...
Aaron's Essays
The Hindsight Game
There are all kinds of strategies for evaluating startup ideas - investors talk about having a...
3rd Apr 2023
There are all kinds of strategies for evaluating startup ideas - investors talk about having a “prepared mind,” others build market maps, I like to think about toys, and we could go on. What everyone wants to do is predict the future. That’s honestly impossible. But we can...
Aaron's Essays
Avoiding Errors in Demo Day Fundraising
I’ll be addressing the topic below along with Alfred Lin from Sequoia and Ilya Sukhar from Matrix on...
21st Mar 2023
I’ll be addressing the topic below along with Alfred Lin from Sequoia and Ilya Sukhar from Matrix on 3/24: https://us06web.zoom.us/webinar/register/WN_qgghYDq4QxCiW9REOOrbmw
It would be challenging to name all the fundraising mistakes that founders make during the many demo days...
Aaron's Essays
There Are No (Absolute) Red Flags in Venture Capital
Let’s accept, for the purposes of this essay, that founders and venture capitalists are engaged in a...
22nd Feb 2023
Let’s accept, for the purposes of this essay, that founders and venture capitalists are engaged in a simple trade. Founders sell business risk for the cash they need to take bigger risks; venture capitalists buy that risk hoping it will one day transmute into reward. Each side...
Aaron's Essays
Generative AI Might Just Save Venture Capital
Originally published in The Information on November 2.
For the past nine months, nearly every...
8th Dec 2022
Originally published in The Information on November 2.
For the past nine months, nearly every investor with a Twitter account, blog or board seat has been beating a unified and constant refrain: The go-go days are done. Founders were being pushed to build 36 months of runway,...
Aaron's Essays
VCs are Scared When They Should be Greedy
I originally wrote this essay for The Information, where it was published on July 6, 2022.
I've...
20th Jul 2022
I originally wrote this essay for The Information, where it was published on July 6, 2022.
I've read a lot of the advice that venture capitalists have given founders on the current state of the markets. Most of that advice focuses on how founders need to adjust to survive the...
Aaron's Essays
In defense of exploding term sheets
There’s a lot of content out there arguing that exploding term sheets—ones that expire after a set...
14th Apr 2022
There’s a lot of content out there arguing that exploding term sheets—ones that expire after a set amount of time, whether or not they’re accepted—are bad. Some of this comes from founders who do not appreciate the pressure; some if it comes from VCs who want to emphasize their...
Aaron's Essays
The hot round fallacy
I originally wrote this essay for The Information, where it was published on Feb 16.
Here's a fun...
3rd Mar 2022
I originally wrote this essay for The Information, where it was published on Feb 16.
Here's a fun little paradox in fundraising: Founders and the media love to talk about how quickly funding rounds happen these days—think about the big, rapid-fire raises...
Aaron's Essays
A framework for choosing what to do
A year ago, I left YC and felt a bit lost about what to do next.[1] A lot of people were pretty sure...
28th Feb 2022
A year ago, I left YC and felt a bit lost about what to do next.[1] A lot of people were pretty sure they knew what I should do. But...I didn't and most of their suggestions didn’t excite me.
As I thought through my possible paths, I realized that I didn't have a useful framework...
Aaron's Essays
Pots of Gold
Here’s a painful contradiction at the heart of spending time on startups: all the good stuff you can...
6th Dec 2021
Here’s a painful contradiction at the heart of spending time on startups: all the good stuff you can create is in the future, but all the patterns you look at to learn what to do are in the past. This makes your brain do funny things. On the one hand, you see how huge things can...
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