Jason Crawford

I stumbled onto a negotiating tactic at age 18, while renting an apartment.

I was looking for a sublet during a summer internship at Caltech.  A student offered to let me take over his lease on an apartment a few miles away, and we were discussing it.  At the time, I was slow to make any decision I saw as important, and this was one of them.  So when he made the offer, I couldn’t make up my mind. The ensuing conversation went something like this:

Me [thinking about it]: Hmmmm. [A pause.]

Him: If you take it, I’ll help you move in.

Me [frowning thoughtfully]: Hmmmmmm. [Another pause.]

Him: OK, I’ll knock $100 off the rent.

Me [eyebrows raised to indicate that this was attractive]: Hmmmmmmmm. [Another pause.]

Him: … and I’ll let you borrow my bike for the summer.

At some point, I realized: I’m winning the negotiation just by stalling. I even held out a little longer just to see what else he would offer me.

He was nervous about the negotiation, anxious to close the deal.  His response was to sweeten the deal for me.  If he had known me better, he might have just waited to let me mull it over.

I don’t recommend this negotiating tactic in general.  (For a good strategic approach to negotiation, see the “principled negotiation” framework explained by Fisher and Ury in Getting to Yes.)  The lesson here is from the other side:  Know when to keep your mouth shut.  When you’re nervous, it’s tempting to fill the void by talking.  This is especially true right after saying something you were expecting a negative reaction to: “We’ve decided not to give you a job offer.” “I’m not giving you a raise this year.”

It’s better to just deliver the message, and then stop.  There might be silence for a few moments while the person thinks and reacts; let it be.  They’ll answer soon enough, and your tension will be diffused.

Chris Dixon wrote last week about the trust- and relationship-centric approach of startups vs. the “legalistic, transactional mindset” in a post titled “Twelve Months Notice”:

For example, let’s suppose you are a two years out of college and have a job at a startup.  You like your job but decide you want to go to graduate school.   The big company legalistic types will tell you to secretly send in your applications, and, if you get accepted and decide to attend, give your boss two weeks notice.

What you should instead do is talk to your boss as soon as you are seriously considering graduate school.  Give them twelve months notice.  Any good startup manager won’t fire you, and in fact will go out of her way to help you get into school and get a good job afterwards.  They will appreciate your honesty and the fact that you gave them plenty of time to find a replacement.

I agree.  I have quit three jobs: D. E. Shaw, Amazon, and most recently Pelago.  Each time, I gave as much notice as possible, usually months.  I told my manager (and sometimes his manager) as soon as I was seriously considering leaving.  To the great credit of all three places (and all of those managers), they were all supportive.  In the same spirit, I’ve always tried to remain a 100% dedicated employee to the very end.

If you’re a productive employee, no manager worthy of his role will hasten your departure.  They’ll want to hang on to you as long as possible.  (You might even find yourself negotiating for how soon you can leave.)  The only motive I can imagine for firing someone in that situation is spite—a motive so petty I’d hate to think I had ever worked for such a person.

Chris stresses that the startup world is dominated by an approach that “relies on trust, verbal agreements, reputation and norms.”  I agree, but many bigger or more established companies take the same approach.  It’s just a matter of taking a broad perspective and a long-term view of what leads to success and reward.  What goes around, comes around—or to put it positively, you get what you give.

The Incredibles is one of my favorite movies, and its director, Brad Bird, is intelligent and articulate.  So a few years ago I watched The Incredibles with director’s commentary. I remember two insightful things Bird said that were relevant to startups.

One of them is a story he repeated in an interview with the Museum of the Moving Image:

It seemed like for years I was throwing a thousand decisions a day into this bottomless pit, and I’d go, “Is anything going to happen with these constant judgments I’m making?” And, “Oh, yeah, we got them, we got them.” So it’s another day, another thousand decisions into the pit—where you’d never hear the splash, either—and it’s just (makes a wind sound). (Laughter) And you go, “Is this movie getting done? I don’t seem to see any…” “Oh, yeah, we got it, it’s getting done.” And, seemingly, nothing happens. Then, suddenly, you get these images, and they’re more complete than you could ever imagine them, and all the lighting is there, and all the details are there. It seems like it was made overnight.

Throwing a thousand decisions a day into a bottomless pit, only to see it all come together much later.  Software can be like that.  Getting more visibility is part of the motivation for Agile development and minimum viable product.

But you can still get that bottomless-pit feeling working towards any large-scale, long-term goal—such as building a product or a company from scratch.  You have this grand vision and it won’t be fully realized for years, no matter how many milestones you hit along the way.  Every day you do small tasks—going to meetings, writing emails, reviewing specs and mockups—and you make decisions all the time, a thousand decisions a day on all sorts of little details.  It’s hard to hold on to the long-term vision and to believe that the mundane tasks you’re doing day to day are adding up to it.

The best antidote I’ve found is to set goals—a hierarchy of goals.  Then I can see how the day’s tasks add up to goals for the week, the week’s goals add up to the month’s, the month’s to the quarter’s, and the quarter’s to the year’s.

Have you experienced the bottomless-pit feeling?  What do you do about it?

(PS: If you liked The Incredibles, check out one of Bird’s earlier, lesser known films, The Iron Giant.)

I have a friend who is a successful real estate developer in VA.  He’s been in the business since probably before I was born.  Recently he gave me some advice about business, a piece of which really stuck with me:  When you’re trying to do a deal, it’s better to get a “no” than a “maybe.”

A “no” is straightforward and frank.  If you’re lucky, it comes with reasons.  That gives you something to work with.  Maybe you won’t get the deal, but at least you’re having a conversation.

“Maybe” could be legitimate, but it’s also what you get when someone just doesn’t want to talk to you.  If they don’t want to explain, negotiate, or even give you feedback, they’ll tell you “maybe.”  Unless you get clear reasons for the maybe and some way to turn it into a “yes” (or even a “no”), you’re going nowhere.

This rings true for me, especially given how VCs say “no”.

Friends have wondered why I’m moving to San Francisco, especially since they know me as a New Yorker at heart.  I researched a handful of cities extensively before deciding, so my choice is based on a lot of data.  For instance, San Francisco has the highest population density of any large city other than NYC.  It’s also home to some of the most educated and high-income people in the country, 2 of the top 25 universities, and arguably one of the top 10 symphony orchestras.

But the biggest factors are qualitative.  First, the Bay Area is the best place in the world to do a tech startup. I say this unequivocally because it is undisputed.  People don’t debate: “Where is the best place to do a startup?”  They debate: “Are you crazy if you don’t do your startup in the Bay Area?”  Paul Graham, for one, says simply that startups would do better if they moved to Silicon Valley.

For the record, I agree with folks like Fred Wilson, who derides the startup hotbed inferiority complex and says: “Not every great tech company comes out of Silicon Valley and you don’t have to be there to be a successful entrepreneur…. You can build a great startup in any of the dozen to two dozen startup hotbeds around the world.”  (So Fred, please don’t call me a Silicon Valley bigot.)

Second, San Francisco is the only US city other than New York that has the properties of a black hole, by which I mean: People get sucked in, and you can’t get them out.  (Ask any recruiter in Seattle.)  And SF has one of the highest costs of living in the US, which means people are paying a premium to be there and still won’t leave.  Moreover, people in a black-hole city seem to be so excited by what’s happening there that they don’t even think or talk about anything outside—as if they are beneath some event horizon beyond which even light cannot escape.

Economics says that when there’s a gravity well that deep, there’s a reason.  I’ve lived in New York, and I know the reason there.  I want to learn the reason for SF.

In the end, though, what convinced me is that I’m going to be a first-time entrepreneur, and I think I will learn faster in Silicon Valley than anywhere else—through exposure to peers, mentors, and the general milieu.  There’s nothing more valuable to me, since I have a lot to learn.

In 49 BC, Julius Caesar—not yet emperor—was in command of an army in Gaul, preparing to march on Rome and seize power.  At the time, part of the border between Gaul and Italy proper was a river known as the Rubicon.  To protect the Republic, Roman law prohibited any army from entering Italy; by crossing the Rubicon, Caesar was making war inevitable.  It is said that as he crossed, he declared: Alea iacta est! “The die is cast!”  To this day, “crossing the Rubicon” refers to committing oneself irrevocably to a bold and risky course of action.

I am now crossing my own personal Rubicon.  In the next few weeks I am quitting my job at Pelago and moving to the Bay Area.  In the next few months I will be doing my own startup.

In making this leap, I am leaving behind a secure, comfortable life.  I’m changing a lot of things at once.  I’m taking on a bigger challenge than I’ve ever known, and more personal risk.  At times I’ve asked myself, “What am I doing?”  But I know this is exactly what I want to do.  Starting my own company has been my primary goal in life since high school.  All of my career has been a training ground or springboard towards this end.

If I succeed, it will be the most rewarding thing I have ever done.  If I fail—at least I will own the failure.  In any case, it will be the adventure of a lifetime.

Alea iacta est!