The Inhabitants of Startup Land

For those of you who may be entering the startup world for the first time, it may be helpful to have some knowledge of the kind of people you’re going to meet. In my short, eight-month journey in Silicon Valley, I’ve met thousands of people in the startup world and had tens of thousands of conversations with them. Yet when I sat down to write this post, I was amazed at how few categories I needed to come up with a decent guide book.

Now, it’s important to note that I am not singling anyone I know out. Everyone who knows me should understand that I have the utmost respect for their style, approach, and dedication. We are all out there trying to make it in Startup Land. I wish everyone I’ve met the greatest success in all their ventures.

It’s also important to mention that these are fuzzy classifications. Most people do not fit squarely into one category entirely or uniquely. Rather, we’re all a blend of different amounts of the categories, with one trait likely being the most dominant.


The Natural

These guys are the rarest of the rare. They just seem to get it all. The idea, trend, design, marketing, implementation– everything. If you ever meet these guys in their brief periods of build up, strongly consider joining their startup. You never know what that weird podcast startup will pivot into.


The Veteran

They’ve been here since at least the first bubble in the 2000s. They usually know a few billionaires by first name, even if they’re not necessarily billionaires themselves. They’ve seen all the players come and go and they have lots of insight to share. These guys tend to be unbelievably generous with their time; it will amaze you how far they will go out of their way to help you.


The Luckbox

The right time, right place, right moment of inspiration. That’s what this group had on their side. They built a startup and quickly flipped it or divested themselves significantly. Now they’ve acquired fuck you money and their confidence often makes it seem as though they have the world in the palm of their hand. Take their advice with a grain of salt– just because they won a hand of poker doesn’t mean they know how to play the game well.


The Tourist

The hype in the press got to this person and all of a sudden they need to be in the game. They will come up with some idea and talk about it… and talk about it… and well, never really build much. They aren’t in it for anything other than the feeling of action. They just want to make easy money, which is the opposite of what a startup really is. You should avoid wasting time with these people if possible. In a few months they’ll have a day job and be on some other new fad.


The Academic

Career academics have a special place in the startup world. They push research boundaries and with no need to immediately monetize they can afford to work on long-term, big ideas. The flip side is that they are the exact opposite of a startup: they need to ensure their work is rejection-proof before showing it to reviewers, they highly value ideas as the implementation is often not that interesting, and they’re fine with imagining potential pain points. If you speak with an academic, understand the world they’re coming from, and don’t expect them to be able to fully understand your world. In their mind, ideas are all that matter– the rest is trivial. QED


The Theoretician

A startup theoretician is someone who goes to all the big insider conferences and loves to talk about things like the Lean Startup Movement, but never seems to convert that knowledge into a successful startup of their own. If you come to talk with them about a problem, they’ll often correct you mid-sentence with a term that summarizes your problem. This can often be a helpful conversation to help you arrive at an innovative solution. The frustrating part with these people is that they’re often unable to innovate because they’re so focused on following the experts. They will often fail to ever launch because they’re still getting user feedback or looking for proper market validation to determine their next pivot point.


The Contrarian

Contrarians are the worst. Conversations with them will lead to nothing but holes that they see in your idea. If you told them you have a search engine and will make money based on displaying relevant advertising, they will tell you it has no chance because so many people use AdBlock that you’ll never get any clicks. They’re typically engineers who spend all their time building systems which need to be rock solid, and that’s awesome, but startups are not engineered. They’re hacked, scrapped for parts, and reassembled endlessly until something sticks. Do not let these guys get you down– they don’t get business.


The Artist

The one thing an artist does not lack is passion. They’re driven by emotion and have a deep rooted connection to how people feel about their work. They usually have a good eye for UI/UX and design, and you can typically spot them via their trendy clothes. Be aware though that they often let other things slide that are more frustrating to engineers, and you may have to pick up the slack for them. They’re not lazy, it’s just how they think and you have to take it as a whole. A good artist will transform your startup’s message from a list of features to a poignant connection with the fundamental desires of life.


The Hustler

No skills except a gift for gab, some elements of manipulation, and (hopefully) an eye for business innovation and execution. I’m personally very conflicted when it comes to this group. On the one hand, I don’t think a major important company will crop up in the tech center from someone with no engineering or design background. There are just too many decisions that are made when scaling for which you need all three skills– understanding people, engineering, and design. On the other hand, I hope I’m wrong because the more awesome companies that are built, the better off we are as an industry, country, and species. If you aren’t great at negotiating deals, marketing, and sales, then you may be able to learn quite a lot from a hustler.


The Computer

Some people in Palo Alto and Mountain View just look and act like computers. The way they dress, the way they walk, the things they say– they are the anti-hustlers. They’re so into technology that I think they lose sight of the purpose of creating new technology: to improve the lives of other people. They generally are excellent hackers but often fall prey to latest-and-greatest syndrome, wanting to jump from Rails to Sinatra to Node to whatever else is hot. If you’re co-founding with this type of person, you need to take a step back at the start, evaluate the technologies which are stable, and then decide along with your co-founder that you will stick to a single stack. It’s also important that you help these people improve at more human-oriented tasks like marketing and design, as it will help facilitate communications with them down the road.


The Hopper

The only thing a hopper is dedicated to is hopping. They jump to a new idea every month or so. In extreme cases, I have known hoppers who can’t hold a job for more than a few weeks without quitting because there is another one they think will be better. The interesting thing about a hopper though is that they usually engross themselves entirely into a project for the time that it captivates them. This can make hoppers useful as early-stage prototypers, since they will enter the project with full belief that it’s the next Google and then leave later on without wanting anything to do with it. I have to confess: I used to be a hopper. It wasn’t a crippling disability, but I would usually dive into a side project and drop it within a month. If you suffer from this illness, the solution is likely a mixture of organization, companionship, and responsibility.


The Grandfather

As opposed to veterans, grandfathers seem to think modern technology isn’t worth their time to learn. They were there for the first wave of the internet, and they haven’t bothered to keep up with the changes. They don’t understand how to leverage social media and in-bound marketing. They don’t understand cloud services or the real value of an API. They can be toxic to a startup, as they usually have other commitments and will slow their contributions by an order of magnitude. Unless they have clear, well-established connections to VCs and you know they can raise money, I urge you to avoid founding a startup with these people.


The Kid

Where a grandfather sees no importance in anything new, a kid sees everything as being new and revolutionary. They have tons of energy and will routinely attend all-night hackathons to play with a new technology or create a new experimental service. They don’t always have a great appreciation for revenue generation or sales, but they understand the power of social media and how it can be leveraged. The key difference between a kid and a natural is that the kid simply loves technology from a young age, not startups, and they may have less self-esteem than an experienced developer. They can be great to co-found with if you have patience to deal with a lower level of independence due to inexperience and lack of confidence.



As I noted in the intro, I don’t believe anyone is entirely a single category. I personally see some of each one in me, but I am happy to hear others’ opinions on that. :D

Also, did I leave out any? If you were going to prepare someone for their move out to Silicon Valley, is there another type of person you would let them know to look out for?

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