Zach Holman

As Someone Who Has Written This Blog Post,

2026-09-16T00:00:00+00:00

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 bootlegs from the 1950s, a sentence you have only said once on the internet fifteen years ago! 1950s bootleg jazz really makes me think about my company’s revenue accelerator program you might be interested in!

It’s a really fucking weird time. Everyone’s tryna do the cold email approach, but AI has made it so insanely easy to grab a few factoids from your bio in an effort to “tailor” their approach to you.

As someone who gets a lot of cold outreach, I can’t tell you how often I get told who I am. “Hi Zach, as an early employee of GitHub who invests in developer tools…” is a phrase I see almost daily now. No real fucking human being talks like that. In fact, I think that might be the only remaining Turing test we have left. Are you telling someone about their own current job and/or something they did fifteen years ago? TURING TEST DENIED

Real people latch on to real shit. “Hey, I remember meeting you in the bathroom of a Kraków conference during the Obama administration, we were drunk and talked about plants, do you want to invest in my company?” You definitely could have made that up — my hatred of plants is so complete as to prevent me from ever calling you out on it — but it’s such a weird combination that it works.

What’s worse is that the generic AI route usually bombs out spectacularly, too. I’ve had MULTIPLE recruiters send me an email where they first tell me I live in San Francisco (oh cool I didn’t know), that they themselves love San Francisco, and they make sure to sit and get a coffee at Fisherman’s Wharf every time they visit the city for work. Brother, no living soul has sat and gotten a coffee at Fisherman’s Wharf and has enjoyed their time there, much less decreed it such a spectacular experience they’d GO BACK AND DO IT AGAIN.

ahhhhh I’M TOO ANGRY TO FINISH THIS BLOG POST OR EVEN HAVE AN LLM WRITE ME A NICE CONCLUSION FUUUUUUUUUCK GO WRITE SOME REAL HUMAN SHIT TO OTHER HUMANS SOMETIME

Probably Won’t Pass You on to Another Investor

2026-08-05T00:00:00+00:00

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 signals from other investors (that they ostensibly trust) that your company wasn’t a good fit for them.
It gives me as the referring investor at a reputation hit because I’m asking this other person to take time out from their lives to look at a company that I don’t even have belief in myself.

That said, I have seen this approach work well. A decade ago I pitched a lovely investor who really liked the company but was worried about a conflict in their portfolio, so they were a pass. But without asking, he proactively suggested a few possible introductions he could make (and then he made them). This was great because it gave him a clean surface area for the other investor (“I like the company, but I’m just conflicted out!”), and I wasn’t forcing him into doing something he didn’t want to do in the first place, so the intro was far more genuine.

That’s really what you’re aiming for: the proactive “…but I’ll still help you out!” Most investors will side with doing that if they think the pitch is truly novel: even if they don’t participate, they still want the aura of referring it to another investor who might. If they’re not offering to do that for you, you’re honestly probably better off talking to that VC cold, rather than getting a not-so-warm introduction.

The Cold Email

2026-07-29T00:00:00+00:00

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 thought doing all of this was pretty silly and a waste of time — didn’t I mention this all before? — but my dad kept saying it wouldn’t hurt to really make it clear I wanted to get into the school. I got in shortly thereafter. Didn’t realize it at the time, but CMU clears something like 1%-10% off the waitlist, so it was indeed more rare than I had realized. Guess it did make sense to reach out about it after all.

In 2010, Chris Wanstrath tweeted about looking for junior developers who knew Ruby (I did) and Java (uh, sure, I could maybe fake it). GitHub at the time was kind of the most clique-y of startups; they had made it clear that practically all hires at that point they had worked with previously or interacted through open source. No one knew who I was, and it was frankly pretty intimidating to fire off this email:

Couple weeks later we met at Hotel Utah and they hired me on the spot. Still don’t know why they did; there were plenty of better programmers of both languages out there to choose from (this is back when you had to type code with your fingers). In hindsight, the company was fairly broke — or at least revenue neutral each month — and a $60k junior developer salary was probably low-risk enough to try. Still, I had reached out and lucked out.

Six years ago I sent a cold DM through Twitter and ended up owning part of a soccer club, which I’ve written about to an excessive degree. That one DM led me on an eventual path to ownership in another soccer club, this time in Serie A, and led to a ton of investments I’ve made in sports/tech and the professional and volunteer work I’ve done across the sport. It has very much become my life’s focus, and it’s not something I would have at all believed you had you told me about it a decade ago. It’s never too late to switch gears.

When cold emails didn’t work for me

This is when the Hacker News commenter or Twitter complainer or whoever will say “well who gives a fuck, it’s just survivor bias”. It’s true; I’ve had a stupid run of great luck in my career, and cherry-picking past results don’t inform future performance. But the difference is I’m also going to tell you all of the cold emails I’ve written that went nowhere and didn’t end up changing my life.

…yeah no; no fucking idea.

I’ve done tons of cold outreach to people I admired, half-contacts I had met once, people who might share interests with me, I’m sure of it. I actually just sent a cold DM this afternoon to someone on Instagram who has a super interesting overlap with me, thought we could have a chat sometime.

But I don’t remember those, not really. It’s kind of the opposite of gambling, where the gambler won’t remember the huge pots won, but they can tell you every second of the bad beat they had in their careers. In this case, you tend not to remember the awkward chat you had with the famous CEO at the meetup, or that one email you fired off three years ago, but you remember the outcome of the things that did go well.

Just do the thing

You can’t win unless you skate to where the puck is going to be buying a lotto ticket.

That is to say: you gotta actually do the thing and reach out and say hi sometimes. It’s occasionally awkward and weird and strange, but it’s usually worth a shot. Standard disclaimer applies, as it does to everything in life, though: actually give a fuck, be interested in the other person, and be genuine. Trust me, I get a ton of cold outreach and virtually all of it I can see through as to whether or not someone’s trying to play me, or is honestly trying to make a real connection.

And the most important part to keep in mind: if you’re reading this and thinking, wow, this is awesome, he’s totally right, I should send that email to Zach right now! That’s definitely not what I’m saying here- leave me alone and go bother someone else.

All jokes aside, the other part of this equation is the recipient. Even though warm job referrals are a fantastic way to hire, I’ve long since decided that no matter what the circumstances were at a company I might run, I’d always accept cold resumes and emails. Kind of a way of paying it forward for the people that did the same for me. Same with cold pitches to my profile on Signed: I’ve invested in many startups that I hadn’t the faintest connection to personally. It greatly expands your own network and helps dismantle blind spots. And it’s just the right thing to do.

It’s also helpful to realize that while you may be sending the cold email today, in another area tomorrow you might be someone else’s cold email. Not every part of life is a linear progression.

So: on occasion, with respect and restraint and genuine good-natured attempts: go out and reach out when it makes sense. Could be good, could be great. And help people, when you can.

There’s No Minimum Angel Check Size

2026-05-01T00:00:00+00:00

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 share. But this putz is tellin’ me you know, uhh, 100 shares? Wrong answer! No! You have to be closing all the time.

Boiler Room

We’re not in the boiler room anymore, but angel has changed a lot in the last decade.

Recently one of my portfolio founders was talking to me about fundraising and said a VC frowned on his $1k minimum check size in the round, said that he needed to up that to $25k or $50k (or more!)

There’s a few historical reasons for this suggestion, and they’re all wrong today.

Small checks don’t muck up the cap table

First one was the biggest: Section 12(g) of the Securities Exchange Act of 1934 (roughly) meant you had to go public once you hit 500 shareholders. This dinged a lot of companies like Facebook, since, you know, it wasn’t 1934 anymore and the financing economics behind venture capital had changed dramatically.

When you hear “clean up the cap table”, a lot of it comes from this historical point of view, that it becomes problematic having so many shareholders of a company. That’s gone for a couple reasons.

The JOBS Act (Thanks Obama!): 2012’s JOBS Act expanded the amount to 2,000 “holders of record”, or 500 who weren’t accredited investors.

RUVs, SPVs, Rollups, oh my!: The biggest change lately is that of roll up vehicles. AngelList kicked off a new approach that let 250 individual investors get rolled up into a single entity on your cap table, so even if you add 250 small checks in your round, you’re still only effectively adding a single “shareholder”.

There are a few drawbacks of using a roll up vehicle for the investor themselves: the main one is that you’re entering through an intermediary, usually one controlled by the founder themselves, so theoretically you won’t have direct influence on your equity or voting power. In practice I’ve found this to be never relevant for angels: by definition of being a small check, your equity power isn’t going to hold much weight in the first place, so who cares. You looking for the return exposure, not legal power over the company.

Small checks don’t water down your attention

Another thing that I’ve heard come up is that you’re suddenly going to have more people who care about your company to respond to and talk to, and I guess that’s a pain and a real drag on your time and company. If that’s the case: why the fuck did you take their check in the first place??

Seriously. Someone being excited to give you feedback on your investor updates is a good thing. And from a technical level, they’re just another BCC on the monthly email. (You are sending regular investor updates, right?)

I’ll give you another tip: things can change, and it’s super fine if they do. For example: the investors that help you out from your pre-seed days aren’t necessarily the same ones that will help you out around your Series D. A number of my later stage companies switched from “let’s chat frequently” to “we’ll chat every now and then”, and… that’s great! I know I’m a better fit early on, and I want them to keep focusing on the wild fuckin’ returns they’re bringing to my shares. So no, I don’t see an issue with ruining your attention.

You don’t need to turn the screws on someone for a few grand

I’ve increased my check size a few times over the years because a founder has requested it. Every single time I’ve regretted it. I don’t think this has explanatory powers, but I wanted to point this out because I’m still angry about each of those, lol.

If you’re doing a purely pre-seed angel party round, sure, I could see the desire to try to move someone from a $1k to a $10k check, but if you have any institutional checks in the round they’re going to dwarf the angels anyway… so who cares?

You don’t need an actual check size at all

I was going to do the standard “hey, $1k is a fine minimum check size”, which is kind of the standard “we’ll take anyone!” amount founders mention these days, but I don’t think that’s right. The correct answer — to borrow from Boiler Room — is zero.

By that I mean this: think hard about the person you’re talking to and if they can have a real impact on your business. When you start talking about check sizes, you realize $1k is a pretty fucking easy barrier to clear in terms of billable hours: do you think you can get $1k in value from this person as an advisor, as a networker? That same question can go for zero: even if they don’t pay you anything, would you give up a few grand’s worth of a SAFE now in order to meaningfully benefit from this person’s experience and network?

It’s a classic “grow the fucking pie” problem: smaller slice of a way bigger pie is the whole ball game when it comes to startups. You want more good people on your boat, and if you’re worried about a couple thousand bucks when you’re also raising a couple million from a traditional fund or whatever: what are you even thinking?

Party rounds are back in, baby

The more the merrier. Startups are already a very lonely road: there’s no reason not to bring some new friends to join the experience with you.

Signed: A Portfolio for Investors

2026-03-24T00:00:00+00:00

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 this crowd might not have their finger on the pulse of technology after all. HMMMM.

Anyway, I always had some crazy shit in my head that I wanted to see built, and after a couple hundred angel investments and five different attempts (Numbers.app => Airtable => Notion => bespoke app => Notion), I finally build the damn thing: Signed launches today. Sign up at signed.com.

Spreadsheet++

Hey, I’m not knocking spreadsheets. They’re incredible (even for non-profits, too). But I always hated distilling an entire angel investment and my entirety of working with the company down into a single row in Excel. There’s so much more to it!

What’s more, I’d wager 95% of the angel spreadsheets I’ve looked while building Signed are absolutely trash. It’s actually been pretty jaw-dropping, at times; I know some investors running multi-million dollar portfolios through effectively a single row of “company” and “amount invested”. Even “date invested” is hard for some to track down, much less return profile, IRR, PPS, and all sorts of other things you can derive from your financials and the company itself.

You can’t improve unless you first measure. So Signed helps me manage a ton now, and accordingly I’ve never had this much visibility into my own portfolio.

One of the things that’s really bothered me is that investing is inherently a social activity, but it’s done almost entirely behind closed doors: private introductions, cold emails, even literal closed doors to the meeting room. AngelList had a concept of social activity around their offerings, but years ago they’ve fucked off to chase funds and SPVs. So ironically we didn’t even have a List of Angels really anywhere (not sure what we’d call it).

Anyway, now we do: Signed has public profiles and woooooo boy do I have a lot of really cool shit I’m ready to build on top of this in the very near future.

Private markets? Everyone’s an investor.

I’ve been building Signed over the last year or so, and it’s been an interesting time to build something in the private markets: startups are continuing to wait ever-longer durations to make it to IPO, and secondary offerings have caused some big dilemmas for investors and employees alike. None of this is looking like it’s changing any time soon, and it’s a good time to get a handle on all this- even if you’re an employee. Free accounts’ll let you track your employee equity just like an investor does.

And you should: startup equity is a lottery ticket… until you hit it big and then you realize thinking it as a “lottery ticket” was doing you a disservice the entire time. It’s an investment, and you should treat it as such.

ship it 🐿️

So Signed is live now! It’s been in beta for a few months, and though we just have dozens of early users, Signed is already tracking $75M in equity, which is a pretty exciting start. So much more yet to build (and write! — there’ll be plenty of new posts on my blog and the Signed Blog this year as well.) Have at it! signed.com

The Tools of Angel Investing

2026-02-27T00:00:00+00:00

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 bad if you want to do things with the money at your bank. (Don’t worry; if you don’t want to do anything with your money, banks are still bad.)

I have burned through so many banks over the years. First, you start with one of the Big Four banks, because that’s what you bank with and you figure hey, I have money here, let’s send it to someone. There’s your first mistake: it seems banks employ scores of teams specifically to prevent you from sending wires or ACHs. (This was facetious when typed, but honestly… probably not wrong, considering the fraud they incur from this broken system.)

Some banks will bury transfers behind administrative debris: first you have to create a Company record, then a Person, then you have to add their bank details with pasting disabled in your browser because they assume typing 9+17+17 numbers by hand is going to be less error prone than pasting it directly from your wire instructions.

You’ll also see process limitations: sometimes you can only send three wires a month, or only receive three wires a month. Or maybe they’ll cap transfers at $1,000. Or I’ve had one bank straight up not allow me to send transfers at all unless I call in and repeat the numbers by voice to my banker.

I had many other points to add here, but this is not designed to be an anti-bank screed (you’d be here reading for forever). Suffice to say, American banks don’t want you to move your money.

Eventually I just realized it’s best to actually go with a bank that is designed to transfer your money. I ended up going with Wise (normal link and referral link if you want some fee-free transfers or something). Wise was built specifically to transfer money quickly and cheaply globally, and it turns out they’re pretty good at it. Their security is quite good (but not overbearing), they let you upload a PDF of wire instructions and parse the account numbers and amount for you, and generally it works great as a sort of “slush fund”, where you just use it as a holding account before sending out or receiving it elsewhere. They also have a kind of sudo mode like we built at GitHub where you’re not constantly getting hammered by 2fa requests.

Other possibilities: Mercury normal link and referral link, and Rho.

Legal entities

One of the things you can play around with as an angel is how you invest in companies, legally. There’s a few different approaches:

Invest as yourself, under your own name (easiest)
Invest as your trust (easiest for estate planning)
Invest as an LLC

I’ve done all of them (and then some), for varying reasons. The first two are fairly straightforward: I’ll cover the latter briefly.

One thing I loathe as being a more serious angel is that you get lumped in with all the other angels who might invest in one or two companies a presidential term but still call themselves an “angel”. You see a lot of funding rounds of “We raised from Sequoia, Hustle Fund, and a bunch of angels!” It’s that “a bunch of angels” which is kinda shrug.

Something I’ve done in the last few years is incorporate Tifo as an LLC, in an aim to group my investments somewhere between traditional venture fund and occasional angel. It’s nice to have a separate brand you can expand over time. For incorporating I just used Doola, which I’m not a huge fan of but it exists as an option. If I did it again I’d probably just use Stripe Atlas for the LLC- I’ve incorporated a c corp with them a number of times over the years and it’s just not trashy like Doola and all the other registrars are. There are some concerns with investing out of an LLC if you want QSBS treatment; give it a research prior to jumping into things.

One other more advanced approach you can take: I also have a trust for Tifo which specifically invests out of my Roth IRA. My dad, of course, thinks this is a terrible idea, but it’s not a meaningful amount of money, and it’s something I can afford to risk. The benefit of this is twofold: any gains you make are tax-free, and it also involves far less reporting overhead (to the point where it’s actually pretty alarming how much you just… don’t have to report to the IRS; makes life much simpler). My Roth investments are primarily short-to-medium term bets in later stage companies, with the hope to compound faster and with (slightly) less risk than a pre-seed company I might normally invest in.

There are some real concerns with this approach, though: QSBS treatment might save you a lot of taxes, anyway, so that underlines another motivation to look towards later-stage (ie, non-qualifying) companies for this. You also do have some reporting and bookkeeping concerns — it’s not just totally the Wild West here. And there are some critical laws around self-dealing which is a huge no-no.

It’s also a pain in the ass to do right now. You want a “checkbook IRA”, which allows you to write checks for qualifying investments as you see fit. Best I’ve spotted is Rocket Dollar, who tries their best to break their platform every couple of days (it’s currently not allowing sign-ins for the last week because… reasons?) But at the end of the day it does let me make these Roth investments, and hopefully in another decade I’ll have billions of dollars in it like some other truly evil people in the Valley.

Portfolio tracking

Once you shoot a wire over to a company, you really should track its performance over time. I just launched Signed for this reason. No, I’m not going to make a harder sell here. If you’re interested in seeing more, go check it out; it’s fucking awesome.

Meeting notes

The other thing I wish I did more religiously during my first few years of investing was taking a lot more notes during pitches, during 1:1s with portfolio companies, and keeping track of things better. I’ve used various CRMs for this over the years — now I used Signed, of course — but the point is to use something. The more founders you meet, the harder it is to pull these conversations to front-of-mind years after you made your initial investment. There’s too many beers in life to keep track of them all in your head.

Turns out I suck at taking notes, though, both in school and also as an investor. I also feel like a dick, typing away as I go, instead of actively listening. I’m not the first investor by any stretch to suggest Granola, but it really is the best at this point- let it transcribe your call, it’ll mix it with your own notes you want to focus on, and then you can dump the transcript into Signed or your CRM or however you want to do it going forward. Did not think I’d ever be a “notes” guy, but here we are.

So that’s what I’m using currently. Probably will change by tomorrow, though, given how fast things are moving these days. (And if you’re building those new things… hit me up.)

Taking Money off the Table

2025-10-30T00:00:00+00:00

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 emails and conversations with others I run across in the startup world. It’s a decision can be annoyingly agonizing. And there’s a lot of conflicting advice out there, each with different motivations behind it. I’ve added to that, too, with lots of advice over the years of “look at all the alternatives in front of you and make an even-headed decision”.

Anyway, fuck it, here’s the bottom line: take that money, queen.

Gambling with your life

I’ve found it helpful to look at your life as a gamble: a set of probabilities that add up to whether or not you should make a decision a certain way. Assuming you’re in this situation, you might be looking at a windfall of, say, half a million to tens of millions of dollars. That’s wildly lucky, and can be life-changing money.

Two massive motivators in this decision:

It’s way easier to make more money when you already have money.
Successful startups are an insane mix of timing and luck — no matter what people who sell online courses will tell you — and if you’re at a point where your imaginary gains are truly life-altering… you’ve already won. Now: try not to lose.

I’m here to tell you: don’t fuck it up. It’s easy to assume two things, because we’re Startup People who are Bold and certainly will Change The World (by increasing query performance by 6%):

we assume that this will be just the first of many correct startup decisions we will make and every four years we’ll be faced with this decision
that the startup we’re at will only go up and to the right because that’s all it’s ever done and surely it won’t face hard times both internally or externally

Successful startups sometimes fuck up. I interviewed at Zenefits about a month before the first bad press came at them- back then it was one of the fastest-growing companies of all time. One of the execs interviewed me and guaranteed I’d become stupid rich if I joined. It was obvious to them they were all going to be gazillionaires in no time at all. I came away with dozens of utterly insane stories I continue to tell over drinks, and frankly was horrified at how much of a clusterfuck everything internally was. But you talk to them and they were all convinced they could do no wrong. (Except for head of infrastructure- he was the most interesting person I interviewed with and we had a fantastic discussion about how fucked up the infrastructure was. Figures that the earliest to know something are the ones who see it break the most.)

All of this to say: it’s easy to become delusional while at a startup — in fact, you could argue that the best startups have that cult-like delusion built into their DNA. But things can change. Or the external structures can change. I don’t have to tell you that tech is in a bubble right now; everyone knows it, everyone knows it’s going to pop, but no one knows when or the extent of it. There have been hundreds or thousands of startups over the decades, staffed with the best and brightest, with revenue, with customers… and they’ve still bitten the bullet. That’s the game. So don’t look a gift horse in the mouth; take the horse’s wallet instead. (Sometimes my metaphors don’t always land.)

It’s a forcing function

You reading all this and thinking it doesn’t apply to you? That your startup is c r u s h i n g it and that by selling, you’re leaving so much money on the table? Good. One of the reasons I wrote this in this way is to act like a forcing function: get you to be horrified at the thought and make you critically analyze if holding on to your stock makes sense or not. It’s like the advice of flipping a coin to make a decision, and as the coin is in the air you’ll learn which decision it is that you’re hoping it will land on.

I will say this, though: I did take a tender offer after I left GitHub, it was a wildly stressful decision, but I have zero regrets today. I took something like 10% off the table, which had a positive impact on my abysmal emotional health at the time, and had GitHub ultimately eaten it, I would have had at least something left to show for all the work I had put into the company.

Amusingly enough, this post itself stemmed from conversations with Billy Gallagher, the founder of Prospect, one of my angel investments. They do scenarios and projections of early equity stakes, and I basically told him that I’m too horrified of doing the retroactive math behind taking the tender and dealing with all the stock fuckups GitHub subjected us to. It’s probably a large number. But I don’t think about it at all today. Would have been helpful at the time, sure, but the stress is a product of the time, and likely not one that will stick with you forever… if that helps you make these decisions.

I also found it helpful to realize something logistical, too: the money you take today is, you know, still money. You can invest it, diversify it, grow it. The exponential growth of startup equity makes the more linear — but still compounding — growth of “normal” investing feel like you’re just losing out, but you’re still compounding that cash. It doesn’t just disappear.

You can afford to not be perfect

So yeah- all of this is good to think about. Run the numbers. Model different scenarios. Get a real understanding of the trade-offs here.

Sometimes it’s helpful to “get permission” from someone — anyone — though. Like, that it’s acceptable to make this tradeoff. When GitHub got acquired, one of the best pieces of advice I got was: you can afford to not be perfect. There’s this weird pressure out there that every single financial decision needs to be optimized for every little bit of performance… but sometimes you can miss the forest for the trees with that. You can also drive yourself mad, and forget why you’re doing all this in the first place.

I’d also be remiss to not mention that this isn’t entirely a “rich person problem”. I’ve known many paper millionaires who were functionally broke: they had school debt, or were putting their partner through school, or had kids with costly needs, or they were responsible for multiple families or generations who were relying upon them. Liquidity in startups is increasingly harder to come by these days. Life is constantly about planning for the future, whenever that thing might come. Sometimes it’s helpful to think about today, too.

Shipping Calendearing

2025-09-29T00:00:00+00:00

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 your own itch. I’m going to just invent the term “Partner-driven development” for the times where you’ve said multiple times you’re going to write something and then your wife/husband/partner keeps complaining that indeed, that was bullshit and why haven’t you built the thing you said you were going to do years ago yes I realize software is sort of hard but you keep saying it would be easy to whip together and yet here we are, not in fact using it?

As a calendar sicko who spends too much time thinking about calendars over the last decade, I sync like a dozen different calendars to my phone and desktop: a personal calendar, a calendar for a nonprofit I work with, a couple calendars for Tifo and Signed — yes, Signed is also shipping shortly — various soccer calendars for Oakland Roots, Tottenham, Dortmund, USMNT & USWNT, events I’m going to from Luma and Partiful, and so on. And yeah, my wife Monica did, on occasion, give me some well-deserved gruff for making it pretty difficult to track when I have something going on without having to sync all of those calendars to her own calendar anddddd… it was a mess.

Your endearing calendar

So it’s something I always wanted to build in a Do One Thing Well app: add the URLs of all your calendar feeds and dump out a single feed for my wife to subscribe to and get visibility on my schedule. So that’s what Calendearing is. You get it? It’s an endearing calendar! Sometimes typos while writing code turn into realizing a .com is available and the hellhole that is Naming A Company ends up being three minutes instead of six months.

It’s $30/year, and merging calendars is all it does. Nothing more, nothing less. There’s no crypto, no advertising, no VC treadmill, no AI models powering the thing. WYSIWYG.

I love angel investing, I love building venture-scale products, but I really miss side projects, too. My start to the industry was 25 years ago when I built Good-Tutorials, which housed the most tutorials for Photoshop and other software in the world for well over a decade. I read well over 100,000 submitted links over the years (and yet, I still never became very good at Photoshop; imagine that). I sold it not too long after joining GitHub, but I do miss those days of having something small and just yours to work on and learn from. And god, I haven’t had this much fun just building since Rails came out twenty years ago.

So yeah, if you have calendar problems, well, I have the solution: don’t build a calendar. Oh and then use Calendearing if it’s of interest to you.

Losing Money is the Point

2025-07-21T00:00:00+00:00

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 new streaming service.

No; losing money is the fucking point.

Econ 101

You’re not “losing money”, of course: you’re investing. (Yes, I realize that line sounds like a meme, but stick with me here.) The money doesn’t just go up in smoke- it gets invested in staff, infrastructure, materiel, and so on. It all comes down to a single bet: more investment in the organization today will mean larger returns tomorrow. That’s it; that’s the thing the average person seemingly doesn’t understand. You’re now smarter than average (which, depending on your take on the general state of the world, could mean a lot to you, or still be embarrassing).

The thesis behind that single bet is the important one, of course: you’re assuming you’re operating in a business where early success can be replicated in a later stage organization. If you can, the thought process is simple: invest in the business and you’re going to make more money, particularly if you have enough cash to grow the business in the meantime (either through your own pockets or through outside investors).

There are myriad reasons why that wouldn’t be the case, though: the market might not be big enough (in which case you can’t keep expanding your sales), your company’s hierarchy or process might not scale at the same efficiency as before, competition might snuff you out, or sometimes you’re just unlucky.

That’s why there are so many Series B+ funds out there whose job it is to basically pour gas on a fire. Much of their focus is entirely on unit economics: the company might be losing money overall, but have they proven their base case out? The most obvious example of this is Uber: by the time they IPO’d they were losing billions of dollars a year… but they were able to reach profitability in certain mature markets. That made it pretty obvious that raising more money made sense: as they developed more markets, the overall business would become healthier, and most importantly: when they reached profitability it would be at much higher profit levels than if they took a slower route without outside capital. And eventually, that’s what happened.

I’ll take anybody’s money if they giving it away

Sports in general is a pretty good example of this phenomena, which is why the WNBA stuff pissed me off so much this morning. I originally wrote about it through my ownership experiences with Oakland Roots: sports clubs tend to be extremely cash-hungry and require a ton of resources just to survive year-to-year. But that’s largely mitigated through valuation increases.

To take the example of the WNBA, again: just between last year and this year, valuations of those franchises grew, on average, 180% year-over-year. (For novices, something growing 180% in a year is one of those “pretty good” investments to have.) There’s additional positive signs — huge new broadcasting deals, growing expansion fees (which is American sports’ sterling example of socialism at work) — but the valuation increase is the most interesting to look at.

Valuations are a really powerful tool that ownership can choose to wield. There are a couple different ways to leverage a higher valuation: you can use it to secure more debt for the org (through loans, future cash flow lending, etc), and you can also peel off minority stakes. If your team goes from $1B to $2B, hey, it might make sense to bring on a new minority owner for $100M. You still keep majority ownership, but you get that $100M back in the company to grow the pie even more (hopefully beyond the point of the equity you sell).

Red is fine

For certain companies, with easy access to external cash and a clear growth pattern, yes, staying in the red is fine. That’s not the case for all companies — your kiddo’s lemonade stand probably doesn’t need a $45M capital infusion. Unless it’s really fucking good, in which case send me a case, sounds delicious. But yeah, for a lot of venture-backed companies, or sports organizations, or other companies where you can afford to put more cash into the business for a larger longer-scale outcome: red is good, embrace the red. And pay your players.

Nontraditional Red Teams

2025-02-03T00:00:00+00:00

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! It’s an odd experience, turning into one of those startups who advertise on 101. Some sort of weird fucked-up sign of maturity and/or sufficient VC dollars. Particularly for a company whose product only exists In The Cloud… seeing real-world analogues is very surreal.

So Marketing worked on it, ran it through design, chatted on some plans as to what it should look like. If I recall, the GitHub thread on it was a couple weeks old, and Cameron McEfee put out a final “I’m going to send this to the printers at the end of the day, so speak now or forever hold your peace!” Some few-dozen people had seen it at this point so it probably was fine.

Anyway, I looked at the last iteration around the same time as Rick Bradley did and we each were like… uh-oh that looks like goatse. Are we sure we aren’t goatse-ing all of San Francisco traffic for a few weeks? Seems rude.

Cameron dropped a “holy shit” and got it updated it prior to it hitting the printers. He also put a kind of “dick check” in the general design shipping process for large launches at GitHub- check for various genitals, meme-ability, and really any sort of ways the new work could be used in unintended ways.

I mean, the last thing you want is to have teammates work on something for months and users end up ignoring all their hard work because the new logo looks like a booty or something.

It sounds totally goofy, but it’s not a bad idea to have someone in an antagonistic mindset to make sure you’re not shipping something awkward, insulting, or inappropriate through your visuals.

Finally, internet shitposters have a valid business use case.

Someone with an ad blocker

Ad blockers can be somewhat contentious: on one hand it’s good to support websites whose access might be free-of-charge; on the other hand, so many of these websites are fucking terrible, with ads and popups and unclosable interstitials.

But some of your users are going to use ad blockers; there’s no way around that. So have some asshole on your team constantly piping up if you break navigation with various ad blockers turned on. Yeah, there’s some political aspects here — who blocks the blockers? — but every time a site inexplicably doesn’t work because someone made it so a file include or piece of HTML wrecks your entire site is one of the most rage-inducing aspects of modern sites out there, particularly if there aren’t any ads on the site in the first place.

Someone with a password manager

Look: I have a lot to say about sessions and signing in to a product, but suffice to say: there will be password managers for the foreseeable future and holy shit how do you all get the simplest sign-in form so wrong all the time?

Like, at its basic form it’s just a username and password. I get — sort of — layering on all this other shit like magic links and 2FA and enterprise sign-in, but so many dev teams don’t even get the basic form right: they do something custom in a hair-brained way so that 1Password or other password managers don’t auto-fill the form. (Yes, some of that is because 1Password itself has turned into some sort of deranged software that breaks if you look at it, but you get the idea.)

So someone on your team should use a password manager. I mean, you all should, of course, but for the love of god at least get one person on the team to pipe up with “why doesn’t my auto-fill work on our site?” And then fix it.

None of these are like, major blockers: people will work around broken forms or websites, and drivers will drive by your phallus on the highway. But they’re pretty easy to prevent. The main problem is that when you’re building a new feature you have so many other things to worry about… which is why having a kind of “red team” can be so helpful, to come at it with fresh, antagonistic eyes.

Anyway, just wanted you to think about this as you build your products! If you think it’s helpful, I’m just about to send these stickers to the printer- let me know if you’re interested in grabbing one.