Sometimes You Just Have to Ship
I’ve been in this software racket, depending on where you start counting, about 25 years now. I’ve been fortunate to work on a lot of different things in my career—embedded systems, custom hardware, shrinkwrap, web systems, software as a service, desktop, mobile, government contracts, government-adjacent contracts, startups, little companies, big companies, education, telecom, insurance, internal tools, external services, commercial, open-source, Microsoft-based, Apple-based, hosted onvarious unicies, big iron, you name it. I think the only major “genres” of software I don’t have road miles on are console game dev and anything requiring a security clearance. If you can name a major technology used to ship software in the 21st century, I’ve probably touched it.
I don’t bring this up to humblebrag—although it is a kick to occasionally step back and take in the view—I bring it up because I’ve shipped a lot of “version one” products, and a lot of different kinds of “version ones”. Every project is different, every company and team are different, but here’s one thing I do know: No one is ever happy with their first version of anything. But how you decide what to be unhappy about is everything.
Because, sometimes you just have to ship.
Let’s back up and talk about Venture Capital for a second.
Something a lot of people intellectually know, but don’t fully understand, is that the sentences “I raised some VC” and “I sold the company” are the same sentence. It’s really, really easy to trick yourself into believing that’s not true. Sure, you have a great relationship with your investors now, but if they need to, they will absolutely prove to you that they’re calling the shots.
The other important thing to understand about VC is that it’s gambling for a very specific kind of rich person. And, mostly, that’s a fact that doesn’t matter, except—what’s the worst outcome when you’re out gambling? Losing everything? No. Then you get to go home, yell “I lost my shirt!” everyone cheers, they buy you drinks.
No, the worse outcome is breaking even.
No one wants to break even when they go gambling, because what was the point of that? Just about everyone, if they’re in danger of ending the night with the same number of dollars they started with, will work hard to prevent that—bet it all on black, go all-in on a wacky hand, something. Losing everything is so much better than passing on a chance to hit it big.
VC is no different. If you take $5 million from investors, the absolutely last thing they want is that $5 million back. They either want nothing, or $50 million. Because they want the one that hits big, and a company that breaks even just looks like one that didn’t try hard enough. They’ve got that same $5 mil in ten places, they only need one to hit to make up for the other nine bottoming out.
And we’ve not been totally positive about VC here at Icecano, so I want to pause for a moment and say this isn’t necessarily a bad thing. If you went to go get that same $5 million as a loan from a bank, they’d want you to pay that back, with interest, on a schedule, and they’d want you to prove that you could do it. And a lot of the time, you can’t! And that’s okay. There’s a whole lot of successful outfits that needed that additional flexibility to get off the ground. Nothing wrong with using some rich people’s money to pay some salaries, build something new.
This only starts being a problem if you forget this. And it’s easy to forget. In my experience, depending on your founder’s charisma, you have somewhere between five and eight years. The investors will spend years ignoring you, but eventually they’ll show up, and want to know if this is a bust or a hit. And there’s only one real way to find out.
Because, sometimes you just have to ship.
This sounds obvious when you say it out loud, but to build something, you have to imagine it first. People get very precious around words like “vision” or “design intent”, but at the end of the day, there was something you were trying to do. Some problem to solve. This is why we’re all here. We’re gonna do this.
But this is never what goes out the door.
There’s always cut features, things that don’t work quite right, bugs wearing tuxedoes, things “coming soon”, abandoned dead-ends. From the inside, from the perspective of the people who built the thing, it always looks like a shadow of what you wanted to build. “We’ll get it next time,” you tell each other, “Microsoft never gets it right until version 3.”
The dangerous thing is, it’s really, really easy to only see the thing you built through the lens of what you wanted to build.
The less toxic way this manifests is to get really depressed. “This sucks,” you say, “if only we’d had more time.”
The really toxic way, though, is to forget that your customers don’t have the context you have. They didn’t see the pitch deck. They weren’t there for that whiteboard session where the lightbulbs all went on. They didn’t see the prototype that wasn’t ready to go just yet. They don’t know what you’re planning next. Critically—they didn’t buy in to the vision, they’re trying to decide if they’re going to buy the thing you actually shipped. And you assume that even though this version isn’t there yet, wherever “there” is, that they’ll buy it anyway because they know what’s coming. Spoiler: they don’t, and they won’t.
The trick is to know all this ahead of time. Know that you won’t ship everything, know that you have to pick a slice you actually do, given the time, or money, or other constraints.
The trick is to know the difference between things you know and things you hope. And you gotta flush those out as fast as you can, before the VCs start knocking. And the only people who can tell you are your customers, the actual customers, the ones who are deciding if they’re gonna hand over a credit card. All the interviews, and research, and prototypes, and pitch sessions, and investor demos let you hope. Real people with real money is how you know. As fast as you can, as often as you can.
The longer you wait, the more you refine, or “pivot”, or do another round of ethnography, is just finding new ways to hope, is just wasting resources you could have used once you actually learned something.
Times up. Pencils down. Show your work.
Because, sometimes you just have to ship.
Reviews are a gift.
People spending money, or not, is a signal, but it’s a noisy one. Amazon doesn’t have a box where they can tell you “why.” Reviews are people who are actually paid to think about what you did, but without the bias of having worked on it, or the bias of spending their own money. They’re not perfect, but they’re incredibly valuable.
They’re not always fun. I’ve had work I’ve done written up on the real big-boy tech review sites, and it’s slightly dissociating to read something written by someone you’ve never met about something you worked on complaining about a problem you couldn’t fix.
Here’s the thing, though: they should never be a surprise. The amount that the reviews are a surprise are how you know how well you did keeping the bias, the vision, the hope, under control. The next time I ship a version one, I’m going to have the team write fake techblog reviews six months ahead of time, and then see how we feel about them, use that to fuel the last batch of duct tape.
What you don’t do is argue with them. You don’t talk about how disappointing it was, or how hard it was, or how the reviewers were wrong, how it wasn’t for them, that it’s immoral to write a bad review because think of the poor shareholders.
Instead, you do the actual hard work. Which you should have done already. Where you choose what to work on, what to cut. Where you put the effort into imaging how your customers are really going to react. What parts of the vision you have to leave behind to build the product you found, not the one you hoped for.
The best time to do that was a year ago. The second best time is now. So you get back to work, you stop tweeting, you read the reviews again, you look at how much money is left. You put a new plan together.
Because, sometimes you just have to ship.