Insider Insights on Recent YCombinator Companies, San Francisco's Warranted and Unwarranted Doom and Gloom, and More!
Stretch Four Insights Volume 56
Hi All,
I am happy to be back to my regularly scheduled program — after spending nearly a week on the east coast with my family and friends through last Wednesday, I am finally back in my flow. It was good to spend the holiday with the family, but we felt relieved getting back to San Francisco with the little guy being on the road for six nights.
This week I want to highlight two articles, some insider insights I got on YCombinator companies, and my call for apologies from so many spreading doom and gloom online about San Francisco.
Let’s dive in.
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Quote of the week
Home run seeking was an issue even before the birth of my second kid when there was more time in the day. After my latest was born, this tendency really started to undermine me. With time and sleep shortened, it was easy to fall off schedule. Holding out for a large article often meant a total absence of routine or pattern. Some of the delays yielded questionable choices. -Ethan Strauss, All Hail the Model
Chart of the week
Articles
Replacing my best friends with an LLM trained on 500,000 group chat messages (Izzy.co)
I’m Thrilled to Announce That Nothing Is Going On With Me (The New Yorker)
Arrest made in SF killing of Bob Lee — tech exec’s alleged killer also worked in tech (Mission Local)
Final Thoughts
Startup to watch — JumpWire
I learned about this company during a demo day sponsored by Rutter. This product has a chance to solve a hard problem that many companies are facing when it comes to maintaining security protocols. W are experiencing some of those assessments now at ModernTax and it is no fun.
Y Combinator had its bi-annual pitch last week — I talked to multiple founders who participated.
Each founder's story was different. I spoke with some who raised almost $3 million on about $17,000 in annual recurring revenue (ARR).
A friend of mine disclosed that he raised nearly $7 million at a $40 million valuation after 50+ investor meetings.
Other founders did not fare as well and disclosed that it is difficult to raise more than $500,000 from YC.
This week, The Information wrote a piece on some founders complaining about YC's decision to end their Continuity Fund and the heat is already on Garry Tan.
Upcoming Events
I have been invited to demo our ModernTax 2.0 product for seven minutes at the Finnovate Spring Conference in San Francisco in May.
Plugs
The Stretch Four Podcast will be releasing two episodes per week soon. Keep an eye out for them on your favorite podcast players, such as Apple and Spotify.
Call for Guests: If you are a founder, a high performer, or a fellow Substacker with an interesting story or know someone who does, feel free to reach out to me directly at matt@stretchfour.co.
Call for Sponsors: If you are building a B2B brand and would like to be featured in our newsletter or podcast, please check out this link and I will contact you to learn more about your company.