This is Kevin here writing this week. Danielle and I are back from Hawaii and adjusting to the Fall temperatures in Colorado. While we’re both taking time off between startups, it’s been noticeable how work pulls you back in even though you know you need a break. It’s been mostly me writing the past 2 weeks, so let me know if we’re doing a good job of keeping the quality bar high and the writing on point.
Engineering Newsletter Update: last week we previewed an upcoming newsletter focused on engineering content. Several of you are interested, and I’m working on v1, but want to make sure we can keep the quality high. Right now I’m culling together a list of 100+ feeds to pull the best content from, but we may need even more since great engineers tend to write infrequently. If you have anyone you know who’s written great posts in either startups or engineering, just reply to this email and let us know.
From the Operators
Justin Jackson of Transistor.fm takes a sobering look at how long it will take to grow from $781 MRR to a living salary, and questions whether venture scale critics like Jason Fried of 37signals have misled bootstrapped founders in “Bootstrapper’s paradox”
Ammon Bartram and Harj Taggar of Triplebyte recently guided CTOs through the recruiting journey that is ahead of them. They took a comprehensive look at the recruiting ecosystem without overly selling their own service. You can learn from their hard earned lessons in “Building an Engineering Team”
Rand Fishkin of SparkToro points out that highly trafficked sites like Google, Facebook, Reddit, Instagram have become insular and shouldn’t be blindly relied upon to send you traffic in “The Powerhouses of the Internet Are Turning Hostile to Websites”
Amjad Masad of Repl.it gets a last minute YC interview, even after Rick Rolling the entire partnership in “Rejected Then Recruited: Our Journey into Y Combinator”
From the Investors
Fred Wilson of Union Square Ventures celebrates 15 years of publishing his blog this week. He also sat down with Chris Dixon from a16z for a far reaching conversation on AI, crypto, and where we are in the history of the software industry. Easily one of the more thought provoking podcasts I listened to this week.
Hunter Walk of Homebrew cautions founders seeking bridge financing to expect the possibility of a flat round in “Second Seeds: The New Normal But Know This…”
Joanne Wilson of Gotham Gal Ventures recounts the an early career story of standing up to a bad manager in “Be Tough but Be Yourself”
Barry Eggers of Lightspeed Venture Partners shares his recipe for fund construction, sparing many first time VCs from mistakes that will come to haunt them when they raise fund II, in “VC Firms — How to Build an LP Base for the Long-term.”
Martin Casado of Andreessen Horowitz urges founders who are raising to preemptively calibrate their phase of growth for investors in “Aligning Startup Metrics with Stage of Maturity (Beyond Labels for Fundraising Rounds)”
Sammy Abdullah of Blossom Street Ventures outlines how to hire an investment banker for M&A, something too few founders proactively learn about, in “Negotiating with your investment banker”
This Week’s Picks
Last week I recommended the Internet History Podcast, but I could tell from the click through count and my own hasty writing I didn’t do a good job describing it. When I first discovered this great work by Brian McCullough, I was glued to my earphones for days catching up on old episodes. It is an incredible trip down memory lane if you grew up in the 90s, and often gives you an “aha” moment as you see what was really going on behind the curtains. I hope you give it a listen if you haven’t already.
Connections by James Burke
Anyone that works in tech and hasn’t read this book is in for a surprise. Each chapter of the book starts out at the dawn of civilization and follows a chain of an invention taking you all the way up to modern day by the end of the chapter. For example, the Jacquard loom of 1804 was an inspiration to Charles Babbage who built one of the first mechanical computers in 1822. American inventor Herman Hollerith came across Babbage’s difference engine later that century, and build a machine for tabulating the 1890 census. His company would be acquired by a conglomerate that would become IBM. The in depth story in series of inventions is more interesting than anything I can summarize here.