Our ol’ grandpappy had it tough. Back in his day, when he wanted to build a new startup, he’d first spend months coveting the right venture capitalist, undergo hours of interrogations about his planned “agile development methodology” while being assaulted with steaks and strip clubs, diligently select the right lawyers to incorporate the company, and then he’d carefully spend a year or two assembling a crack team of multi-decade tenured employees from Oracle and Deloitte so they’d have just the right chance at cracking the $100k ARR mark by the time Java 1.4 dropped. You already know the joke…
It’s a great time to be the main character in Memento. Back in 2000, Leonard Shelby had a hard time functioning in society because he had no memory of who he was. But if Memento took place today? Hi Leonard! As someone who once was a Coffee Expert at Starbucks for six years — boy, I just love their Pumpkin Spice! — I’d like to talk to you about your SOC 2 compliance! Leonard, I was so moved reading about your condition. Your resilience really inspired me. That never-give-up attitude is exactly why I think you’d love our outbound sequencing tool! Hey, Leonard! I love how you said you like jazz…
This is one of those personal preferences that might differ from investor to investor, but: no, I probably won’t intro you with another investor if I’ve already passed on your company. A lot of venture capital is full of wishy-washy bullshit human feels over reals. It’s an odd way to manage a market worth trillions, but it is what it is. When I refer a company to another investor, without fail one of the first things they’ll ask me is: did you invest? This is a problematic question for a few reasons: It immediately puts your company at a disadvantage because they’re already getting other…
Three of the biggest changes in my life all stemmed, in part, from cold outreach. Originally I was waitlisted at Carnegie Mellon. Getting waitlisted is like, being the first loser: you’re good enough to be in the topic of conversation, but they make it clear that you’re not good enough to actually get accepted. My dad had me next day air an additional essay about what I was working on at the time (I had built Good-Tutorials, which was the largest tutorial website on the planet, so that was something different). I also included a bunch of other material and things about me and my senior year.…
I remember one time I had this guy call me up, wanted to pitch me, right? Wanted to sell me stock. So I let him. I got every fuckin’ rebuttal outta this guy, kept him on the phone for an hour and a half. Towards the end I started askin’ him buying questions, like what’s the firm minimum? That’s a buying question, right there. That guy’s gotta take me down. It’s not like I asked him, what’s your 800 number? That’s a fuckoff question. I was givin’ him a run and he blew it. Okay? To a question like what is the firm minimum, the answer is zero. You don’t like the idea, don’t pick up a single…
Awhile back I asked my friend Leah Culver about how she tracks angel investments, because I was just getting into angel investing and it seemed weird that everyone just had some shitty spreadsheet setup to keep track of all this stuff: Anyway, her answer was “a spreadsheet”. And that was the same for all the others I asked then, too. That was seven years ago. I always figured all these rich angels and VCs who were deep into futuristic next-generation technology would spur some clever tool to track all of their holdings at some point, but that ain’t happen. It’s almost enough to think that…
Part of the annoying thing about angel investing is that you’re ostensibly investing in CUTTING EDGE FUTURE STARTUPS who are about to BRING THE FUTURE TO YOUR FACE and in order to do this you have to go through some of the worst software and processes on the goddamn planet: banks, and laws. Some cool stuff remains, though. Money EUROPEANS AVERT YOUR EYES FOR THIS SECTION Thank god we got all the Eurovestors to skip this section, because it’s going to be a disaster of our own American™ making. Our banking system is trash. I don’t have to tell you this; everyone knows it. But it’s particularly…
Recently I had a long call with an old friend who was facing an age-old predicament that I’ve been seeing more and more these days: Lucked out, worked hard, employer is crushing it, and now she’s sitting on a large amount of paper money gains at her startup Company does a tender offer, either buying their stock back or allowing a third party to come in and buy shares Employees might be allowed to sell, say, 10% (or whatever) of their equity So here’s the question: do you sell, or do you roll the dice and risk it longer? I took a tender offer on my early GitHub shares, and it comes up a lot in…
For when you have too many calendars Once upon a time I built a calendar and then wrote an exhaustively long talk about working with time, timezones, calendars, and everything in between. For a few unrelated reasons we ended up not shipping the calendar, but in general, as I mentioned in the post: Zach, whatever you do: just don’t ever build a calendar. Anyway, I built a calendar again! Okay, technically I got away with only tangentially building a calendar this time around, but it’s the thought that counts. Partner-driven development There’s dogfooding where you write software to scratch…
It’s mind-boggling how many in the general public don’t understand this, so let me rant about it for a bit: many companies are designed to lose money this year. That’s the fucking point. Today’s main character energy is the news of WNBA players wearing Pay Us What You Owe Us shirts during the All-Star game. The knuckle-draggers on social media immediately clutched their pearls, saying “ohmygod the WNBA lost $40M last year so players should really be paid zero dollars, not given a raise!!111” You see this all over the place, like all the stories recently about Apple “losing” $1B a year on it…
Most developers know about red teams: a specific group of people chosen to be the antagonist to your system, trying to sniff out vulnerabilities in your code or organization. Basically, like Sneakers, or the annoying plotline in The Newsroom season two. (Someone should have really red team’d Sorkin himself on that one.) There’s a few other concepts of a red team I think that every development team should have some exposure to outside of the traditional cybersecurity angle. Someone to look for dicks Once upon a time, GitHub was very excitedly looking forward to shipping our FIRST BILLBOARD!…
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