Bullish: How Business Is Like Dating

Business is a lot like dating. Like cold-hearted, competitive dating among people who don’t love each other. In other words, like awful, awful dating.

Once upon a time, when I was considering moving to New York, I looked for jobs. A Director of Marketing position was available at a company I’ll call QuixoticIdea.Com. I was an unconventional candidate — I’d never held a “real job,” but had run a company for about five years despite my relative youth — so I wrote what I remember to be a pretty persuasive email regarding some marketing ideas I had for QuixoticIdea.

The CEO of the company got back to me right away. He wanted to do a phone interview. Cool. During the phone interview, he asked me a lot of really detailed questions about my ideas. He said he’d get back to me about maybe doing an in-person interview.

I followed up, implying that I was coming to New York “anyway,” and would he like to meet? He agreed. (Of course, I hadn’t been planning to come to New York “anyway,” but I also hadn’t been planning to ride my bike past Ben Silverstein’s house “anyway” in 1994, yet implying otherwise totally led to making out on his parents’ porch swing).

Also, I was broke. I printed my MapQuest directions (retro!), packed my best pinstripe outfit (paired with the black heels I wore to prom!), and spent half my net worth on gas to get to the interview. Again, the CEO asked me really detailed questions about how I thought the site should be marketed and how QuixoticIdea might actually start charging money for its quixotic idea. I answered these questions, and the CEO wrote down my answers on a legal pad. I thought it went very well.

I drove back home and waited … and waited. I sent polite emails, but not too many. It became apparent from my emails with the CEO that QuixoticIdea wanted me … but didn’t want to be responsible for my moving to the city. After all, what if it didn’t work out?

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So, I moved to the city, figuring that if the job didn’t work out, I’d start another company. I moved into a room for rent in East Harlem. I was now really, really broke. Once the CEO heard I was in town, he wanted another “interview.” Who does an “interview” in a park? The same person who does a first date in a Starbucks, that’s who. Someone who wants to make it very clear that We Are Keeping It Casual. He came prepared with extremely specific questions about internet marketing. I tried to give good answers that ended with the implication that only I could actually execute such a plan. I realized, while sitting in the park giving free consulting, that I was being booty-called … for my mind.

I realized that QuixoticIdea wasn’t about to commit anytime soon. So I tried to put the company out of my mind. Maybe see other companies. Maybe I didn’t need a company at all! Maybe I’d be my own company.

It’s not hard to start a company with zero dollars (okay, maybe forty dollars). Making a company profitable might be another thing, but it’s not hard to start a company. Business books will often imply that you have to do all kinds of ridiculous things to start a company. Here are some things I typically haven’t bothered to do:

1) Trademark anything. If you own the domain name and operate primarily on the internet — well, plenty of people have put this off at least until their companies were paying them enough to buy food.

2) Become a corporation. Many people do this to protect themselves from lawsuits. However, if you’re a one-person operation and someone wants to sue you, they’ll totally sue you personally anyway, because it’s pretty impossible for a one person operation not to “pierce the corporate veil,” such as by mixing personal and business finances, accepting business checks in your own name, and otherwise just not really being a real corporation. If you’re going to be a sole proprietor instead of a corporation or LLC, you can file a Fictitious Name Certificate for $25 in NYC, or similarly small fees elsewhere in the U.S.

3) Printed bullshit. Because it’s not the ’80s. You can get some $9 business cards from Vistaprint if you really want. But it can totally wait until your company has bought you some groceries.

4) Professional branding. I mean, Squarespace templates are really nice. They have a logo generator. Even if you want to make a great argument for the value of a branding professional – well, your business is going to change a lot in its early months or years, as well it should. You need to constantly iterate in order to provide what your clients actually want. Maybe your first business idea isn’t exactly it, or the buyers aren’t who you thought they should be. No matter how amazing a professional branding job is, it’s a waste to apply it to a business that doesn’t quite know what it does or for whom (and by “know,” I mean by collecting actual money).


(Usual disclaimers: I am not a lawyer, and there are, of course, perfectly good reasons to trademark and incorporate, and if you don’t, you could be one of the unlucky few who has something horrible happen to you! Choosing not to trademark or incorporate is sort of like choosing not to pony up for health insurance when you’re young, healthy, and broke — you could get hit by a bus, yes, but plenty of us make these kinds of decisions anyway, thereby horrifying our risk- averse relatives).

So, I started a company by choosing a business name, making a website, and browsing Craigslist until I found (this was easy — I had several offers to choose from) a company willing to barter desk space in an office, including WiFi, phone, and the use of their mailing address, in exchange for several hours per week of marketing assistance. This arrangement also had the added benefit of allowing me to claim my first client.

Once I had settled into this comfortable marriage of convenience, I contacted QuixoticIdea. “Hi there, CEO! Just writing to let you know I’ve opened up MyNewCompany, a boutique internet marketing firm. My new office is right off Union Square! I’d still love to work with QuixoticIdea and put some of those ideas we discussed into action.”

Of course, everybody wants you once you’re already taken. I wish that I had Jessie’s girl, you know?

The CEO got back to me right away. He had already called the owner of the company (who, I later learned, was really hard to track down) and he was ready to make me an offer. He literally said, “Wow, when we heard you’d started your own company, we realized we really needed to lock you down!” He asked for a proposal (ha ha, “proposal”). I wrote my own job description and suggested what my salary should be. It was a pie-in-the-sky number I’d settled on after searching Salary.com and deciding that even numbers are prettier. I ended up with an offer for about 80% of that number, which made me gratified that my guess had been on the mark (or rather, a little higher than the mark, which, I am told, is how a person bargains).

My relationship with QuixoticIdea did not last forever, of course. But I learned a lot, developed an aversion to certain revenue-free business models, and bought a bunch of cool shit.


Here are a few principles of career success that are a lot like how you would date if you were kind of cold-hearted:

1) Everybody wants you more when they think you’re in demand. Start a company or give off the aura of a successful freelancer, get “clients” through barter to make your business look in-demand, and play up the freelance gigs and client relationships you do have.

2) Conversely, though, companies want to think that you’d drop all that and “marry” them if they were willing to commit. If you got married, of course, you’d have to break it off with anyone else you were seeing, and you might break some hearts; many companies consider it a bonus to hire someone who will no longer serve their competitors, or whose tiny company will thereby fold. I’ve seen numerous cases of small companies hiring someone who then closes her freelance business, and the hiring company gets to claim that it “bought” the employee’s company (which in real life might mean a small signing bonus for the new employee). Even starting a company that never makes any real money (but looks good on the internet) can help you tremendously.

3) Look for a new lover before you’re going to need one. (Again, that’s a little cold in your real dating life, but this is a metaphor). Most people gets jobs through their friends and contacts. Uploading resumes to strangers through online forms is sometimes one’s only option, but you don’t want to be in this position late in your career. You want to be well-known enough in your field that when you become available, someone snaps you up right away. Or, you want to have enough smart, accomplished friends that you can switch fields easily, with their help. So, while it’s not nice to advertise your awesomeness as a potential mate whilst you are in a relationship with someone, it’s absolutely good practice to do exactly that while you’re in a job. After all, your employer is totally seeing other employees.


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