Hustling, Grinding, and Building

Here’s a tweet I saw the other day that made me — as the kids say — “LOL”.

Touche. This is a really, really annoying part of today’s cult-of-entrepreneurship. You can blame it on internet culture, or venture capitalists, or the way the media covers and informs the public about these things, but either way the end result is often a incredibly clumsy grouping of unrelated challenges into a single, stupid bucket. You don’t have to be an especially cynical person to roll your eyes at the idea of how “tech companies”, “startups”, “SaaS businesses”, or any number of vaguely defined groups of things are supposed to behave, because like any other vaguely defined group of things, correlation is easy to find and causation is extremely difficult to pin down.

What everyone from famous people like Elon Musk and Peter Thiel, to a million different poorly credentialed Forbes contributors, have managed to do is convince themselves and any number of hangers-on that the solution to every problem is intelligence, or their own self-identified hard work. If you buy that logic, their success is not only immediate validation of how intelligent and hard working they are (because problems can only be solved by intelligence and hard work, and they solved a problem), but validation that they can solve any problem they put their mind to (because, again, problems are solved by intelligence and hard work, and in this system, they have proven themselves to possess one, or more likely both, of these things).

In many ways, we have a tendency to do this with strategy as well as leadership, which is slightly less annoying but arguably more dangerous. I get this a lot when people want to tell me how to do marketing work, and get frustrated with its alleged complexity — here’s how company X did it, company X is successful and respected, why aren’t we doing what company X does?

If you are a frequent reader or someone who works with me, you can probably guess my extremely predictable response. What is company X selling? Who are they selling it to? What kind of resources do they have? How much risk are they willing to take on? Can we connect the success of this thing company X does with company X’s success? And finally, are there any major differences between these answers for company X, and for us? Because if there are, company X may not be what we want to emulate. Nobody really likes this answer, but for the most part I think it helps people to generally start to understand the complexity of the issue if they haven’t already.

Now, at a slightly more abstract level, I do think you can group business challenges (or any sort of productivity one, to be honest) into categories that can help you start to think about the best way to address them. These are more philosophies than they are tactics, but that’s ok — you have to start somewhere.


I define hustling as the frantic pursuit of any positive opportunity you can identify. Hustling is really important when you’re first starting out with an idea, because that’s when it’s the most unproven, and when it’s most likely that what you’re doing is worthless and requires you to radically change. It’s also important (although often times more depressing and less exciting) if you’re running out of money.

Some businesses are always about hustling, at least in theory — my guess is that commodity traders and venture capitalists are almost always in a hustling mode, running from thing to thing trying to maximize the chance that they’re in on the ground floor for the next great opportunity. People who are great at hustling are often thought of as “entrepreneurial”, even though building anything other than a ponzi scheme often requires that hustling eventually evolves into something else. But there is something really magical about professionals who can drop into hustle-mode when the time is right — those people are usually one (or more) steps ahead, and they can be a lot of fun to be around.


Grinding is the repetitive, iteratively improved act of day-to-day execution. If you start grinding before you’ve sufficiently hustled, your best case scenario is that you get really good at executing a less-than-optimal business. That’s not a necessarily a terrible thing, but it’s an obstacle to reaching your full potential, and the worst case scenario is that you get really good at doing something worthless. The later scenario is not uncommon, and that’s why “grinding” through your job sounds like a bad thing.

Still, grinding is important — essential, even — to building anything other than a hilarious frat-house startup, and contrary to what you might think, a ton of learning occurs during grinding. In fact, while you learn large, existential things while hustling, most of those things are useless in the long term, because you end up hustling on to something else. Things you figure out while grinding, on the other hand, get baked into your core business operations and help you indefinitely. Grinding is often thankless, but essential, and personally, I think most mid-stage startups fail or end up missing their opportunity not only because they failed to grind, but because they assumed grinding would be pretty straightforward and wouldn’t require a lot of focus.


Sometimes you hustle around and find the right opportunity, but there’s no way for you to successfully grind it into a real business. This is usually because you either don’t have an essential part of the necessary grinding process, or because it doesn’t exist yet. Either way, this means it’s time to build, whether that means creating a product, improving a technology, or changing the way your organization works and solves problems. Building is very rarely a direct revenue-generator, so it’s hard to get companies to agree to do it, and even harder to get them to agree to make it a priority over hustling and/or grinding (“you can build as long as we are hitting our numbers” is one I’ve heard a lot). The truth is that regardless of your cash or goal situation, the time may come when you simply can’t go any further until you build something, and that means you have to find the time and resources to do it, or else you die.

What these modes have in common, and what makes them different

If I were a betting man, my money would be on the average CEO responding to this breakdown by explaining that “the interesting thing about our business is that we really need to do all three”. This is, of course, a total leadership cliche and is not interesting at all.

Still, to some degree it’s often true, especially if your organization is big enough to have multiple major challenges. But that doesn’t let management at any level off the hook when it comes to setting the tone for the company as a whole, or for setting that tone on a team by team (or employee by employee) basis and not sending mixed messages about how each person should be approaching their job. Maybe inside sales is grinding as they improve their process for handling inbound leads, and business development is hustling as they go after new verticals or try to find someone to buy a new product. Maybe the back-end team is hustling as they try to figure out a cost-effective way to store all this data they weren’t expecting to be responsible for, while the QA team is building new tests. Maybe Bob is grinding through highly standardized marketing campaigns and looking to optimize results, while Barbara is trying to build an account-based marketing system and get it up and running.

The point is, these are really different workplace attitudes that have their time and place depending on what you’re trying to do. If you’re looking at a certain part of the business (or sometimes even the organization as a whole), and people in leadership have fundamental disagreements over whether you are hustling, grinding, or building, you have what I would consider a fairly important alignment problem.

One other thing that’s really interesting about these three very different mentalities is that none of them have a monopoly on any of the things we value at work, like creativity, or hard work, or discipline. These things are useful in all stages, but do have to be applied appropriately. One person’s idealized vision of hard work is really a form of hustling, and it’s possible they’ll see a highly efficient form of grinding or building as lacking in effort or urgency. Until fairly recently, I personally lacked sufficient appreciation for the subtle creativity that’s involved in effective grinding, or the discipline that comes with an exceptional hustling mentality.

More than anything, I find this type of classification useful to get a sense of why people think they’re doing what they’re doing. If you’re baffled by someone’s priorities, or feel like smart people are doing seemingly dumb, pointless things, it doesn’t take much more than a quick conversation to figure out what kind of mentality everyone is operating in, and where the source of the disconnect is.

Plus, you get to say “grinding” at work a lot, which is fun.