For your weekend pleasure When It’s Over & Helpful Boards [Jared Hecht/GroupMe, Fundera] — Two more great posts from one of my favorite founder bloggers right now. The former is about deciding to sell your company and the emotional journey accompanying the pragmatic one. After selling groupme I once had…

According to the laws of aerodynamics a bumblebee shouldn’t be able to fly, but no one told it, so it does. This oft-repeated fact is, well, absolutely incorrect, but serves as a nice metaphor for ambitious startups. Probabilities suggest they should fail, but, hey, why not succeed? And experiencing an…

Do you know the parable of the Blind Men and the Elephant? The lessons of one’s subjective truth being espoused as an absolute one based on their own experiences carries beyond zoology. So when I tell you what I’m seeing in venture financing these days if you disagree with me…

How Pop Stars Turned NPR’s ‘Tiny Desk’ Into Authenticity Theater [Adlan Jackson/New York Times] — As Stefon might say, music’s hottest club is called Tiny Desk. And it has everything. Gwar, Taylor Swift, Juvenile. NPR’s Tiny Desk has always been wonderful across its 15 years, but is having a specific…

I judge the health of the creator economy by one single controversial factor: ease of access and probability of survival for its participants. That is, if you are someone who wishes to earn a minimum viable living being creative, what is the likelihood you’ll be able to do so? A…

Playing Different (Stupider) Games The Other End Of The Valuation Stick [Kyle Harrison, Contrary Capital] — Kyle puts out a new essay (almost) every Saturday and I really enjoy his consistent and clear eyed POV on venture capital. There’s a group of us who I describe as “in the industry…

“You both have context for this introduction, so I’ll let you two take it from here! I know you’ll really enjoy chatting.” That was the email one of Ethena’s founders sent to me and Melanie Naranjo on 8/21/21, a bit over two years ago. At the time Melania was in…

I love talking to folks with expertise in areas where I’m more basic. Years ago when Philz Coffee started expanding from a single shop into a multi-storefront, multi-city business I found myself in a chat with their CEO Jacob Jaber. Fortunately he was game to answer a bunch of my…

What’s the most important goal for the money a startup spends? If I asked this question to a bunch of different founders and investors I bet the answers would vary. Some would shout one word like “revenue,” “customers,” “team” or even “profitability.” Others might give me formulas like, “LTV:CAC ratio”…