Why are you joining a startup?

Don’t join a startup just for it’s mission. Of course you shouldn’t join a company selling opioids or sugary drinks, that would certainly be a Bad Thing. But do not expect it to affect or shape your experience much at all. The reality of working in even the most compassionate startup is that:

• The mission becomes an abstraction that you work towards, using general purpose tools and structures (e.g. a marketplace is a marketplace and cares about things like GMV and liquidity, regardless of whether you’re facilitating home rentals or dog walks).
• Unless you’re joining as an equal partner or as the primary executive, you will (still, for you ex-finance/consulting types) be working in client services. This time, the client is your founder. And again, what you’re solving for (making the founder happy) might overlap with what you think is most important to the underlying mission, and it might not. Remember, the VC’s invested in the founder - not in the business, nor in you.
• A corollary of the above is that you are making a massive investment in the founder. Depending on if/how much you value your time and your life, you’re investing way, way more than the VC’s did. Are you sure they will be a great manager and leader? Do you want this founder to be the intermediary between you and the mission?

Don’t join a startup as a generalist. And by generalist, I mean any role without specific ownership of, or responsibility for, an outcome on which the company is very dependent for its success. Nebulous titles like “business operations,” “growth,” or anything with “strategy” in the title are likely culprits.

The reasons:

• You’re likely not to own anything important. If it were important, it’d probably have a clear owner already. There’s a caveat, that’s worth addressing:
  • I’ve seen examples of people identifying and solving new problems that arise as a company grows, finding the schlep problems or other dirty work no one wants to do, and crushing it - impressing their bosses and teammates, and providing them a platform to take on new responsibilities.
  • But this assumes 1) that there is in fact growth, growing pains and new responsibilities to come, and 2) that you can identify these (more difficult in remote environment where there’s less casual conversation and complaining), and 3) that new, important responsibilities won’t first go to another shiny new hire or to someone else that’s gotten to prove themselves on a more tangible project first.
• It’s difficult to establish sufficiently important and clear goals and expectations.
  • Job descriptions and hiring managers may emphasize the importance of being “comfortable in fluid environments.”
  • This is hard (and immensely valuable and important) to do life, let alone startups. It’s even harder if you’re 1) in an extremely hierarchical environment in which you’re not at the top, and 2) not working intimately with customers already (which usually gets done by sales or support…if you’re in one of these roles, congrats, you’ve escaped the generalist trap). You may not have the breadth of context to see highly relevant, strategic, greenfield opportunities or the resources and authority to make them your own. Careful you don’t sell your capacity to navigate nebulosity for a discount in a situation where you may not even be set up to succeed.
  • Related to my point above about how the more unequal is the distribution of ownership, the more your job becomes client services: The more “generalist” your role, the more your job becomes client services as well! (And when I say client services here, I’m talking about work that does not speak for itself, and does not itself do anything. For example: a powerpoint deck does not speak for itself. Whereas hitting a sales target speaks for itself - it’s harder to argue about whether you hit it or not.) This is particularly ironic, given that some folks coming from finance/consulting specifically leave client services in order to have more ownership, only to take the most client service-y job: “biz ops,” “biz ops & strategy”.
  • It’d be one thing if you were joining a firm as partner, or a company with a large ownership stake. When you do so, you take extreme ambiguity as the price of upside, ownership, authority and getting to eat what you kill. But without these thin

Now, of course you should be a generalist under the hood at work, and in life! It’s how you get things done resourcefully. But there’s only one official generalist in a VC-backed company, and that’s the CEO. Is the only reason you want to be a generalist is because you don’t want to get your “hands dirty” in sales (the horror! You’d work in sales now) or you’d rather just “keep your options open?”

If you intend to “sell sales as a service” (or some equivalent) to your “client,” now we’re talking…

In short, it’s very hard to build a strong business of one as a generalist. Better not do it.

More speculative - don’t accept the classic VC-backed startup structure as a default mode of working in the first place!

• Imagine building a treehouse with some friends. Or some other group project you’d be excited about. I.e., any situation where you might be excited about the end product and mission, and you’re excited to work those other people. Say there’s 5 of you. You are essentially a 20% owner. Does this still sound fun, and do you still join, if I decrease your stake to 1% (if you’re super outstanding)? Or more likely, 0.5%, 0.3%, or less? The correct answers are:
  • 1. No way in hell.
  • 2. Yes because there are concrete benefits that make it worth it (a) apprenticeship, b) money and time it provides for my other priorities, c) I get to play a specific craftsman-like role in the treehouse-building process that I really enjoy doing for it’s own sake).
  • 3. Yes because I don’t have any better options and the Mafia is knocking on my door.
  • All are solid answers. But in no scenarios is this about the mission anymore. This is the founder’s treehouse.
• It’s tempting to play it forward and think about how your tiny fraction could be a meaningful sum if the company prospers. It’s part of the temptation of joining early - you get equity when it’s less in-demand. But this analysis discounts the realities of having only a tiny ownership stake when many of your colleagues own much more.

Don’t join a “team” in name only. “Team” is often an inaccurate description of the startup environment. It’s a euphemism leaders and managers will prefer to use in order to uphold the fiction that startups are different from “corporate” where you’re just an “employee” (God forbid you become a “business man”) and to hide hierarchy that candidates might otherwise resist. Team implies equal footing. If someone owns significantly more of the business than you and has the power to tell you what to do, they are not simply your teammate anymore.

Think hard about whether joining a startup is really a good idea for you. Let’s not make this the next default, dysfunctional path for smart, energetic people that lack sufficiently-specific ambition.