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 sele...

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...

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...

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 g...

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 bu...

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 fo...

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 coo...

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...

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: Z...

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-St...

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 ...

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I’ve made like a hundred angel investments over the years, and I get the sneaking suspicion that the most successful startups in my portfolios are the ones that talk to their investors. Like, that’s it. That’s the nugget for this post. Holy shit no one can help you if they don’t know you need help L...

Quick little announcement: I’m launching my own kind-of-weird-venture-fund today: Tifo. Over the last five years I’ve been doing a lot of angel investing- I’ve made close to a hundred direct angel investments, and then have made dozens of others through syndicates (which again, I highly recommend as...

I think one of the first signs of “ohhhhh they really fucked up” was seeing the passport number for the barber listed for a national team in last year’s 2022 Qatar FIFA™ World Cup®™. Here’s a quick story of how I spent the run-up to the World Cup last November. If you’re one of those people who love...

You know the old joke… there are only two hard problems in computer science: NAMING YOUR STARTUP. It’s always been hard to come up with a name for a new company, but it feels like over the last five years it’s gotten even goddamn harder. You spend a little time, brainstorm a solid name, discover six...