True Tales Of Love And Startups: Why You Should Date (Even Marry) An Entrepreneur

True Tales Of Love And Startups: Why You Should Date (Even Marry) An Entrepreneur

Lisa Hodes Rosen and Seth Rosen

By Lisa Hodes Rosen

This guest post is a part of a series on the Work/Life balance of young entrepreneurs: Surviving the Startup: Building a Business While Living A Life.

My grandparents were married for 66 remarkable years. As neighbors in Brooklyn, they met at the tender age of 13 and wed five years later. Together they survived The Great Depression, my grandfather’s Army service in World War II, three children and one global marketing business, started by my grandfather, an entrepreneur, after he left the Army and then dropped out of law school. There was little about life that they didn’t claim to understand. Well, actually, there was one thing: why their 30-something well-educated and ambitious granddaughter was still single. Despite my whining best efforts, I could not articulate the very simple tenet accepted by more recent generations as a fundamental truth:

Dating is hard.

Blind dates, coffee dates, JDates, Skype dates, broken dates, haughty dates, sloppy dates, aggressive dates, cheap dates, boring dates, better-off-forgotten dates. And God help you if it’s a good date… then the real games begin. How do you let someone know you’re interested without looking crazy? Social media and smartphones have seriously complicated what was once the simple act of courtship. To make matters worse, the 40-hour work week is practically extinct thanks to our services economy. Having dated (or attempted to date) many different types, I can say with confidence that almost nobody works nine to five anymore. Simply put, we are all very busy.

Given that these challenges cut across professions, I wonder why entrepreneurs have been branded with a scarlet “E” when it comes to dating. In many cases entrepreneurs actually make wonderful significant others, and – dare I say it – spouses. How do I know? I married one.

Don’t get me wrong, everything you have heard about entrepreneurs is true. They are egocentric, self-righteous workaholics who are enslaved by their vision. And man, are they poor. But, perversely, these characteristics actually make them really great (life) partners. Let me explain.

Entrepreneurs want to change the world – and that’s hot.

My husband, Seth, and his co-founder, Mike, both started their careers in real estate, but for years talked about starting a company together. In 2009, after business school, Seth became an avid consumer of custom items like furniture and clothing, and he soon realized that there was no central online marketplace to find custom artisans. He called Mike and several months later CustomMade.com was born. The only problem? Neither had internet experience. Well, that isn’t entirely true: they had both used the internet before. No matter their (dis)qualifications, they set out to change the retail buying paradigm in favor of custom goods. The mere thought that they might be able to fundamentally alter consumer behavior forms the foundation of their commitment to the company (though, in fairness, so does the fear of failure).

If confidence is attractive, then an unbridled belief that one will change the world is striking. It is also incredibly motivating. Not a day goes by without Seth challenging me to think bigger and to work smarter. When I doubt myself, which is more often than I care to admit, he reminds me of CustomMade’s humble beginnings: Seth and Mike thought they could build a marketplace website in a weekend for $25,000. That was three years and $3 million dollars ago. They were very, very wrong, but they figured out how to solve some big problems with guts and horsepower, which are the drivers for many successful people. How lucky I am to wake up to that inspiration every morning.

Entrepreneurs don’t have time to play games.

Everybody says it, He’s Just Not That Into You codified it, but it is hard to believe: a good relationship should be easy with no guessing games. When Seth and I started dating, I was working at a big law firm billing 2,200 hours a year. I was on a big toxic tort case led by a partner who carried an ice ax around the office as a symbol of our litigation strategy. Despite this ball and chain, I still found time to check personal email every so often to see whether my crush-of-the-moment had contacted me yet or trading flirtatious but annoyingly ambiguous texts. Playing The Dating Game was my one non-billable indulgence besides eating, sleeping and going to the bathroom.

Happily, Seth robbed me of The Dating Game drama. As busy as I was, he was even busier trying to figure out his new business. He didn’t have time for any distractions and explicitly said so. The rules were very clear: if he wanted to talk to me, he called. If he wanted to see me, he asked. If he was busy but wanted a raincheck, he said so and he found a time that worked for both of us. And the same was expected from me. There were a few occasions when he accidentally double-booked a date and a business meeting, but in those cases he arranged it so he could do both (but separately), or if he thought my legal input would be useful he brought me along and then treated me to ice cream or drinks afterwards. There were no mixed messages – no “is-he-or-isn’t-he” confusion – because there was no place for it. It doesn’t get easier than that.

Entrepreneurs are good decision-makers.

By the time Seth and I moved in together, I had watched many friends go to neck-breaking lengths to get their significant other to propose. Frankly, it scared me. I didn’t want to resort to an ultimatum or a hit man to force him to put a ring on it. While effective, it just didn’t seem romantic.

Shortly after I settled into his apartment, I did what I thought was the responsible thing to relieve any real or perceived pressure by telling him that we should probably wait a year before we breathed a word about getting married. I had choreographed a whole song and dance about why it was important to make sure that he and I worked as couple living in the same space before thinking about the next step. He nodded in agreement, but didn’t say much. Soon after I found out why: he already had the ring.

Several of my friends were just as stunned as I was at the effortless proposal. What was different here? It wasn’t that Seth loved me any more than their husbands love them. The difference lies in the decision-making process. Everyday Seth has to make decisions that significantly affect the direction of his business. When he makes a decision, he closes the matter and moves on. He rarely revisits a decision for second-guessing. He makes life decisions in much the same way. Once he knew that he wanted to marry me, there was nothing to discuss. He bought a (custom made) engagement ring that he knew I would like and proposed. No arm-twisting necessary.

Entrepreneurs think outside of the box.

Many entrepreneurs are poor, and Seth was no different. For the first two years Seth did not take a salary. He made zero. Zilch. Nothing. I had just changed jobs from a big law firm to an environmental nonprofit, taking a 75% pay cut. And we were planning a wedding. We had to make some sacrifices in wedding planning, but where? Seth decided to tackle the budget cuts because he already had some experience spending scarce funds creatively. CustomMade is always racing against its bank account. It needs to make the biggest bang for the least amount of bucks, which was precisely our goal with the wedding. As an added benefit, Seth had also learned the fine art of sticking to a budget, something his more impulsive bride was not very good at.

Most girls fantasize about their wedding days, and I was no different. As a history buff, my dream was always to have grand affair in a Newport mansion or a castle in Europe. Reality was clearly dictating otherwise. It was Seth who pieced together our master plan over coffee. He had contacts at the Langham Hotel (where we met) who would work with our budget if we had the wedding at an off-peak time. The Langham is also famous for its weekend brunch. Thankfully, brunch is much cheaper than dinner, so we could stay on budget. Finally, we agreed that a small jazz band would be more appropriate than a 10-piece party band on a Sunday afternoon – and cheaper, too. An affordable Sunday afternoon jazz brunch at the historic Boston hotel where we met? It sounded like a dream to me.

Life is never boring with an entrepreneur.

Since starting CustomMade, we’ve been involved in several litigations, re-built the website three times, raised money four times, changed the business model five times, and survived The Great Recession.

There is always something unexpected around the corner. Take the day in the fall of 2010 when Seth marched into my office, a smirk painted across his face. “I have a gift for you,” he said. I responded with a smile. My birthday wasn’t for another week, but gifts always seem to burn a hole in his pocket. He handed me a large envelope and stood over my desk as I opened it, the smile fading from my face. It was a copy of a complaint that had been filed in state court. A former independent contractor had just sued CustomMade, Seth and Mike. The claim was $600,000, an order of magnitude more than we had in the bank. I thought it had been unusually quiet in the office in recent weeks.

For the next six months we fought a frivolous lawsuit. I spent several nights editing briefs, and, while it was exhausting because his company essentially became my second job, it was a storm that Seth and I weathered together. Eventually the plaintiff dismissed his lawsuit and his lawyer withdrew from the case, but not before we spent a ridiculous amount of money on legal fees and forensic consultants.

As soon as the lawsuit wrapped, a fundraising round began. There would be no rest for the weary. CustomMade needed cash and it needed it quickly. “Strap on your seatbelt,” Seth said to me one day. “This is going to get bumpy.” I couldn’t help but laugh. He was just telling me this now?

Although he doesn’t always say it, I know that Seth appreciates my dedication to vigorously defending and supporting his business. Sometimes I think back to my grandparents’ stories about the difficult times they faced as my grandfather struggled to build his business. Perhaps I shouldn’t be surprised that I ended up with an entrepreneur. Maybe I’m attracted to the struggle and sacrifice.

…Or maybe I’m on to something, and entrepreneurs really do make relationships easy and life exciting.

Lisa Rosen is an environmental lawyer by day, and a startup spouse by night. Follow her on Twitter at @Entreprenrswife.