With YC application season coming up, I thought it would be fun to share some tips that can help. Check out our post on the Buried Reads blog.
Quick PSA on Hiring
I just celebrated 6 months of working at Quizlet, and I’ve been loving it. Quizlet helps people practice and master anything they’re trying to learn. Two thirds of US high school students use the app every month, and if you talk to anyone under 30 there’s a good chance they’ll tell you it saved their bacon in high school and college.

Since joining I’ve fallen in love with the culture. Everyone is caring, celebrates success, and knows what they’re doing when it comes to their craft. I’ve also been impressed by how fast the product and engineering teams turn the crank each sprint despite being a relatively large organization.
We’re hiring in product, engineering and recruiting across both San Francisco and Denver. If you are interested or know someone that is, email me directly and I am happy to jump on a call or connect you directly with the position’s hiring manager.
From the Operators
Joel Gascoigne of Buffer deserves a ton of credit for being one of the most transparent startup bloggers. This week, he shares his company’s experience diversifying into three products, and what MRR looks like overtime in Buffer’s Evolution and Expansion.
Tim Chen of NerdWallet sat down with the editors of First Round Review to share lessons learned from the first ten years of NerdWallet. The advice for CEOs that lands the strongest with me: after product market fit, the company itself is the product you work on as the CEO. They should resist the temptation to meddle in product by this point.
Neel Desail of ProfitWell pulls back the curtain on ProfitWell’s data set to show “How is CAC changing over time?” While his approach is a bit cooky, maybe Chamath Palihapitiya is right that Facebook and Google (along with San Francisco commercial real estate) are eating most of the VC money coming from Sand Hill Road.
Nathan Barry of ConvertKit just took a week off to learn to sail in the San Francisco Bay. His video is a fun, light-hearted way to spend 5 minutes this weekend.
From the Investors
Ali Hamed of CoVenture goes a layer deeper into the well-chronicled trend of companies staying private longer in What Will The People of 2040, Wish They Had Been Doing in 2019. He suggests that if Michael Milken were starting out as an investor today, he’d be creating a bond market for late stage startups. If you don’t know about Milken’s work on bonds during the 80s, he’s worth reading about.
Dave Kellogg of Host Analytics shares his advice to potential startup employees in Things to Avoid in Selecting an Executive-Level Job at a Software Startup. Those considering joining exec teams can save hundreds of hours of wasted time and grief with this post.
Jeffrey Carter of West Loop Ventures presages what will happen to Small Investors on The Capitalization Table after institutional investors lead bigger rounds. If you are a new angel investor (or have any on your own cap table), this is a great read to gain a better understanding of the pressures and challenges they face.