Bullish: I’m Starting 12 Businesses in 12 Months, And This One’s About Cats

This December, I spent two weeks in a hotel in Florida, mostly by myself, periodically transferring myself from a chaise lounge by the pool to a spot at the hotel bar, wrapped up in thought.

(See Bullish: How to Have a Staidcation).

I was partly rewarding myself for churning out another educational book last year (I did a lot of work on this), but I was mostly churning away on a BIG PLAN THAT I WILL TELL YOU ABOUT NOW:

This 2013, I am starting 12 businesses in 12 months.

Obviously, it doesn’t have to be one per month, because it is now March.

The Best Place to Invest Is In Your Own Business

Let’s jump back. I’ve written before about investing. Somewhere around 2011, I had tens of thousands of dollars to invest. I put some money on peer-to-peer lending site Prosper.com (see Bullish: Fund Your New Business or Get Started Investing in Startups), where it is doing 12.78% (my accountant laughed and said he has hedge fund guys who come in and brag about 5%, so there’s something).

But is that how I want to spend my life? Turning out education writing that I don’t get royalties or full credit for, and then investing my money in a crowdfunded loan site? Hint: It is not! I want to spend my life making things that function on their own (businesses, movements, ideas that motivate others), drinking cocktails, and appreciating the fine things in life that I personally am only able to enjoy if I have earned them with the sweat of my brow, as they say, which is a gross expression because that’s when my eyebrow pencil ends up smearing and that is really my most essential makeup item.

What’s the best way to invest your money? If you are young and smart and full of mojo (and not wealthy enough to bankroll a diverse portfolio of other people’s startups), the best way to invest your money is in your own business.

Clearly, there are many caveats. Restaurants cost an incredible amount of money to start and have one of the highest failure rates. Conversely, businesses where you offer a service to people you know are the easiest and cheapest to start, but the hardest to make millions from.

All that said, I’m totally sure that the best way for me to invest my money (which, I have to say, has been dwindling since December) is in my own businesses.

So, sometime in 2012, I opened up a Scrivener file with lots of different tabs. I pretended I was my own venture capitalist. I wrote a little pitch (or, let’s be honest, a stream-of-consciousness set of bullet points) for each of my business ideas, as though I were pitching myself on how to best invest in me.


My inner venture capitalist killed a few ideas right away. We will not be renting a fleet of trucks in a seasonal basis for my Christmas tree delivery service, Treelivery.com. An in-home spa service for rich Manhattanites is a better idea, but there are lots of licensing requirements for aestheticians. A cool idea for a blog is not a business. Go back to the drawing board (uh, WordPress?) and figure out how, exactly, that cool blog is a business. Who are the customers and what will they be paying for, ideally on a recurring basis?

I settled on my first handful of ideas.

How I Decided to Start With Luxury Catsitting

From my hotel, I posted some casual polls to Facebook. One of these polls was, “What would the ideal catsitting service provide?” Among the answers: Emails with photos. Lot of playtime. Cleaning up afterwards. No extra charge for additional cats, which seems reasonable to me. Catsitters charging extra for more cats seems like a holdover from the dogwalking business, where walking two dogs is definitely harder than walking one. However, dogs and cats are different in many important ways, a fact which became the basis of a business plan.

I had been thinking about starting a high-end catsitting service since the end of 2011, when I went to Ecuador for a month and paid my building’s official pet care service hundreds of dollars to take care of my cat, Cow. I printed out my instructions and also emailed a copy to the service’s coordinator. I left for Ecuador. DAYS went by with no word from the petsitting service. I emailed the coordinator many times. I finally got word that the catsitter “was able to get into my apartment.” Um, yes. What about my cat?

By the end of the month, it was revealed that the catsitter had been doing the cat food all wrong, did not even take the new cat toys I bought out of their packages, did not stay anywhere near the full 30 minutes he was supposed to (my doorman logged when he came in and out!), and possibly never even saw the cat. When I came back, the cat was alive (my houseplant wasn’t) — hence the two stars rather than one in the scathing Yelp review I left. It was pretty hard to enjoy Ecuador while worrying about Cow.

It seemed clear to me in retrospect that this pet care service was mainly about dogwalking, and that the service had sent a big dude who smelled like dogs into my apartment. My cat is, not irrationally, scared of people who smell like a pack of dogs.

So, I started EntitledCat.

The Many, Many Steps Involved in Starting a Business

Making the website was easy. I did that from the hotel in December.

Setting up Facebook and Twitter, also easy and free. (My assistant did this.) I had this video made, with the assumption that my target market consists mainly of people who, like me, find a kitten licking a glass window for thirty seconds to be extremely compelling.

Hooking up some kind of payment and scheduling system was an ongoing challenge. On the one hand, I marveled at how, ten years ago, if you had wanted people to be able to pay online and then schedule their own catsitting visits, you would have to pay some developers at least $10,000. Today, you can sign up for a service that costs $20-50 a month, and no one thinks any less of your business when your scheduling system says “Powered by MindBodyOnline” (or SalonBooker, or OpenTable) or whatnot at the bottom.

A word to the wise, however: If you plan to keep your upfront startup costs low by using such a service (and believe me, there’s a service for just about everything, including many specific to the pet care industry), it would be best to see what the service has to offer and then plan what you are going to sell around that, rather than decide in advance how you want to sell, and then get angry at people on the phone because their systems cannot accommodate you.

For instance, if you want to start a yoga studio, it would make sense to offer people the ability to pay for classes one at a time, or to buy a 10-pack in advance and get a discount, or to buy an unlimited monthly membership. It might also make sense to offer a credit system, where people buy a package with a certain number of credits, and then you could charge more credits for some classes and less for others, based on who’s teaching, what level, the length of the class, etc. The first of these is pretty much how MindBodyOnline works. The second of these isn’t possible with any of the systems I checked out. Both might be fine ways to run a yoga studio, but the first model allows you to get started right away. The second means you need to hire a team of programmers.

Here are some other things I did:

Obviously, I bought a domain name. I ultimately picked EntitledCat, rejecting runner-up SuperiorKitty once I realized it sounded like a porn site.

Started using 37 Signals‘ Basecamp to organize my various projects with my assistant, Haley. Basecamp kind of changed everything about how we operate. Before that, Haley and I were just sending off tons of emails like dumb seals.

Joined Pet Sitters International. I was sent a large binder in the mail regarding a petsitting certification that would lower my insurance costs. Chapter 1 was about chickens and guinea fowl. There is very little need for chicken sitting in Manhattan. I did learn that the normal body temperature of a chicken is 103-105 Fahrenheit, and that some chicken owners will let you keep the eggs.

Bought insurance and bonding. When you see signs for contractors that say “Insured and Bonded,” have you ever wondered that really means? Turns out “bonding” is a form of protection in case your employees steal or commit other fraudulent acts. Now you know. Buying insurance for a petsitting business was cheap and easy (under $300 a year, and I just filled out an online form and paid by credit card); buying insurance for another business I’ll tell you about later took lots of phone calls, forms, inspections, and ten times as much money, for the reason that that business didn’t fall into any easy categories. Something to keep in mind.

I bought four fresh white lab coats with Entitled Cat embroidered on the pocket. I bought some fuzzy cat pins to wear on the lab coats. Shopping for cat pins on Etsy was definitely the most fun part of all of this. In retrospect, the easiest part of starting a business is buying supplies. I quickly developed a closet full of cat supplies, but without a functioning business model.

The biggest “luxury” component of my new catsitting service is that the cat carer will remove the cat hair from your couch. How will she do that? She’s carrying a shop vac! I bought a small shop vac, along with a laser pointer, several bottles of all natural odor eliminator, and other cat supplies (to be sterilized in Barbicide as needed). These supplies all fit in what is honestly an Eddie Bauer diaper bag, which, I have to say, is a great kind of bag to carry if you want a lot of pockets. What other kind of purse has cup holders?

I pitched this whole idea to the woman I wanted as my first employee. She’s a reliable and delightful actress who does odd jobs and had recently removed a tremendous quantity of cat hair from my couch. She was game. (She actually recommended the model of shop vac.)

Oh, my god, are there a lot of forms involved in hiring someone. I recommend not only involving professionals who do these things every day (in other words, a payroll service), but also leaning on these people for their help in the aspects of the process that do not directly involve them. In short, the sales rep from CompuPay absolutely did know what forms I was supposed to submit to New York State.

Background checks. You can do this for $50 at IntegraScan. (Do all company names now consist of 2-3 words joined together without spaces? IntegraScan, CompuPay, EntitledCat, MindBodyOnline, SpaBooker, BroBodyDouche…)

Warehouse Clearance Sale


I hired a graphic designer to make postcards, and then had BigCheapPostcard send the postcards out via USPS’s Every Door Direct Mail®. Basically, you no longer need a mailing list to do direct mail — you just pick a zip code, and your postcard goes to every address in that zip. This cost about $2,000, including printing and postage.

I also had some smaller cards made for giving out to people who see someone in an EntitledCat lab coat and ask what the deal is. Want to save money on printing postcards if you don’t really need the cards to be mailable, but you also don’t want business cards? You can get any-size cards by googling “club cards.” Mine are 3 x 3 inches and look way better than business cards because squares are equilateral.

A Business Versus a New Job

If you’re going to start 12 businesses in 12 months, they need to be businesses, not just new jobs for yourself (see Bullish: Are You Thinking Too Small?). I never wanted to be a catsitter; I wanted, and still want, to be a customer of an awesome and reliable catsitting service.

This means that I can’t just play it by ear every time a new customer comes in. When I ran my internet marketing company in the early 2000s, every project (making a website for this client, running an online marketing campaign for that one) was different. There weren’t a lot of procedures in place. I talked to every potential client, often for months. I wrote a lot of proposals and got few commitments. Even that kind of business would have been greatly improved with better procedures. (This, in fact, is the topic of the classic business book, The E-Myth Revisited.)

So, one day recently, after I spent eight hours hooking up various technology products with a merchant account, I met with my first catsitting employee. We went over procedures: Once a customer has paid for their Meet and Greet, the coordinator calls to get some basic information over the phone and to set up the Meet and Greet. The carer comes over — in the lab coat, with the company iPad — and asks certain additional questions. The info goes into a database. The customer is assigned a code. Their key copies are put into an envelope identified only by the code, and stored in a secure location — behind a locked door, in a building with 24/7 security. The carer takes iPad photos of the food and litter setup, the cats’ favorite hiding places, and anything else it would be good to remember. These photos are also tagged in the database. (Don’t forget to pet the kitties!)

I sent my employee over to do a test visit with a friend who had volunteered herself and her three cats for this purpose. After the visit, I followed up with the employee and the friend. Everybody likes everybody! The friend recommended a couple more questions to add to our procedures (“Where do the cats hide?”)

My website started coming up in Google searches, which led to an interview with a luxury real estate blog. This hasn’t come out yet.

Stress Keeps You Alive and Makes Gin Taste Better Later

Because my wedding is in three weeks, people keep asking me how the wedding planning is going. Am I stressed out? Well, yes, but good stress keeps us alive. (You know how old people sometimes retire to warm places and then die right away? It was chopping wood in New England that was pumping blood through their paper-thin veins!)

I can now tell you that starting a business — the kind with actual employees and appropriate permits — is about equally as stressful as planning a wedding, with the major differences that people will remember a botched wedding for way longer than they’ll remember a botched startup, but that weddings remove the stress of trying to make a profit, because weddings are all about spending money, and since you’ve already committed to paying for all the crazy expenses of putting on the biggest party of your life, you can just forget about that part and dedicate the freed-up space in your brain to trying to make money from your business and make the world a better place by taking good care of kitties.

Yesterday, my postcard campaign finally hit! For the past week, I had adopted this habit of walking down the stairs, checking the mail for EntitledCat postcards, then walking back up the stairs as a form of exercise. (I live on the 25th floor.) Finally, there was a postcard! Oh, excitement!

I am not above pawing (ha) through the recycling bin in the mailroom to grab a few extras.

That’s a launch.

First published on The Gloss.

80s 90s Vintage Fun


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