The Startup Spouses

I feel like I’m being sucked into some weird entrepreneurial vortex in which I get lost for hours looking at blogs and websites and products from small businesses. When I was a cubicle resident, I hardly met anyone that worked on their own, and when I did it was like my bikini waxer or masseuse or someone who provided a tangible service, and seemed to be struggling a bit doing so. Now that we’re venturing out on our own, I feel like everybody – the peeps at the coffee shop, the peeps who write blogs, etc – works for themselves. I enjoy being a newcomer to this world, but I have to watch myself because I find that I’m so engrossed in observing that I forget to participate. What are my deliverables for this week? What tangible thing am I working on?

I haven’t been this inspired and excited about work in . . .well, ever. The problem is that it’s not translating neatly into production. I’m trapped in happy look-at-all-the-entrepreneurs land, and not getting my own work done.

Maybe this is a question that plagues only the few restless spirits out there, but we’ve been having a long (5 months!) debate about where we should live as we branch out on our own. The debate is wrought with many angles, such as network vs. family, cost of living vs. resources for startups, city energy (+ distractions) vs. suburban withdrawal (+ boredom), freedom to travel vs. stability. Phew. You’re probably starting to see why it’s been going on for months, and why we can’t decide.

Some of the factors broken down:

• People. The people you’re surrounded by are always important, but having a supportive network when you’re starting your own business is key. Right now we live in San Francisco, where thanks to serious job hopping and higher ed, we have a great community of people we know. This network, in combination with the start-up vibe in the Bay Area, makes it a great location to start our business. The downside? All our friends and family are on the east coast.

• Cost of Living. When you’re trying to bootstrap, any way you can cut costs is worth exploring. In San Francisco, we live in the second most expensive city in the country. With two people working, we live in a fantastic neighborhood with lots going on. With only one income stream and working from home, suddenly our small pricey one bedroom is a lot less appealing.

• Energy. What are the things that you need in a city or town to maintain your motivation and enthusiasm for your work? For me, it’s at least one coffee shop with free wi-fi, an academic or intellectual vibe, and a few 25-35 year old up-and-comings. There is this and more in San Francisco. You know where it’s not? Windsor Locks CT, where I stayed with my family in November while finishing my master’s thesis. I did not get much work done at all. No wireless internet, no cute coffee shops. It’s the kind of place where people “mosey on up to the internet”.

• Time. Where are you going to most effectively use your time? Right now we are totally mobile, and it’s really appealing to think of going to Mexico, or living in San Diego for the summer, and Tahoe in the winter. But while we’ve never had the freedom to travel like that before, there’s a danger that all that moving around will cause us to lose focus and not get stuff done. I am notorious for justifying just about anything when there’s a time limit on my stay in a city. But when you’re trying to build a product, suddenly you don’t want what happens in Vegas to stay in Vegas.

So that’s the short list of criteria, but it certainly makes it tough to decide. You can always leave it up to your friends.

Since we’ve started dating, Kris has been coming up with ideas for his own business. Most of these were sketched out on the backs of cocktail napkins over pours of whiskey, and later forgotten in the haze of hangovers and blackouts. The entrepreneurial spirit has been strong within us always, and that’s not necessarily a flattering thing. Kris is motivated to do his own thing because he has ADD and wants to control everything. I want to work on my own because I’m a bitch and have a hard time following orders and systems that are inefficient and don’t make sense (like the ones at every company I’ve worked at).

While we’ve long wanted to work on our own, it does not mean that we were ready to do so. For one thing, we had a lot of growing up and learning to do in our twenties; while it is a decade that has seen many early twenty something CEOs, we are not part of that camp. We also had some maturing to do on the financial front. We both incurred bad debt in college, and had to do penance when we got our first jobs. When our disposable income finally increased, it was very tempting to buy all the toys and food and liquor we didn’t get to have before, like say an x-box 360 and a flat screen TV in one afternoon. Finally, we did not have good time management skills, and it’s not entirely Guitar Hero’s fault. While Kris worked in-house in startup environments, I worked as a consultant part-time and completed grad school, so we worked a lot during the week, and drank to forget on the weekend. OK, fine, and we do play a lot Guitar Hero.

So if you’re a hard-to-work-with, binge-drinking slacker couple with some ingenuity, and are wondering if it’s your time to pursue your entrepreneurial dreams, here are our tips on things to consider:

• Where does your time go? If you use most of your downtime to cure hangovers instead of work on your ideas, then you may not be ready to venture out on your own just yet. After a solid decade of binge drinking, we’re ready to hang up the (vomit) towel and make better use of our time. Which isn’t to say that we won’t be going out at all, but we won’t be hemorrhaging all of our time and money drinking every weekend.
• Are you ready to walk away from the security and comfort of a job? A stable, comfortable income is very nice to have, but it also makes you a slave to working in-house. When I finished grad school, I knew that it was a good time to experiment before I get attached to a title or salary bracket in a company.
• Are you ready to bootstrap? It isn’t easy to go back on a diet of ramen noodles, but it makes it a lot less risky to work for yourselves. Kris earns enough that we can live on one salary while we get started, so we don’t have to borrow money to try out different ideas.
• Do you respect what you each bring to the venture? For couples, it’s important to identify where your skills are complementary, and where you may have potential conflict. It was a long, painful road for us to figured out how to work with each other. A few years ago, we tried to write a sitcom script together, and didn’t get past the opening scene without getting into a huge fight in Starbucks. The problem we had was we each thought our way was the right way, and wouldn’t compromise our vision. Recently, we’ve completed a few fun projects together, and were able to do successfully, because we worked to fulfill one person’s vision with our collective talents. It just takes some experimenting to figure out how to work together.

If you’ve answered yes to most of these questions, then you’re ready to get started. Now pour yourself a drink and start sketching out a plan.