The Startup Spouses

Instead of working for the weekend, we find ourselves working on the weekends. It just seems to be the time we’re able to get the most done. And work seems more fun on the weekend. During the week, Kris is focused on his day job and has trouble changing gears; I struggle with working alone and motivating Monday through Friday. When we’ve planned to commit a weekend to working on our business, our productivity skyrockets and we’re able to reach milestones. If we looked at why we’re more productive on the weekends, I would attribute it to:

•  No distractions. When we plan to work on the weekend, we ignore any calls and requests to go out. During the regular work week, it is harder to avoid all distractions (i.e. boss calling) and sometimes they’re welcome (i.e. mom calling - phew, I can take a break). 
• Incentives. We try to compensate for staying in on the weekend by cooking nice meals and drinking wine. We plan our menus early Friday and stock up at Whole Foods for the weekend. Monday through Friday, it feels too indulgent (nevermind time-consuming and expensive) to think about food so much. And it would perhaps be concerning if we started in with the wine on Monday afternoon. 
• Interaction. Fueled by wine and devoid of distractions, we’re able to talk and brainstorm freely. While we work 3 ft away from each other, we don’t often have extended periods of time during which we can explore and plan. 
• Scheduled breaks. On weekends, we take breaks when we want, either to watch a movie or workout. There is more pressure during the week to mimic the 9 - 5 schedule, even though our schedule is fairly open. 

Given the success we have working on the weekends, it’s worth experimenting and trying to implement some of the “weekend” tricks during the week. 

I had an appointment today for a physical, which I haven’t done in over three years. As I waited in the waiting room and then the exam room for two hours, I had plenty of time to think about how life’s necessities get in the way of work. This week, in general, I lost a lot of time. We had an accountant appointment Tuesday, after which I had to sadly revisit all our receipts from 2007. Then I realized last night while writing/watching the Daily Show that the battery in my laptop died. Which means I’ll spend another afternoon this week at the Apple store. I certainly don’t mind visiting the cute guys over at the Genius Bar, but it’s another day lost.

My rant about getting all these boring necessities out of the way is significant to the self-employed because we think about time differently. Now I schedule appointments during the day because I hope I will have more options since I don’t work 9-5. I make time to do organizational tasks, like filing or sorting bills. I also spend a lot of time during the day preparing healthy meals and exercising. While it is nice to pay extra attention to myself and attend to oft-neglected tasks, it also keeps me from my main work.

If I worked in an office environment, I would have tried to do my taxes online, and upon failing, given up and hoped that I never got caught for tax evasion. I would never go to the doctors or any other appointment, which explains why it’s been so many years since I’ve been in the first place. I would ignore my mail and let it accumulate until we have people over, at which point we’d hide it in a box to never be seen again. I would exercise less, eat unhealthily, and save chores for the weekend. Sure, there are those people who have busy jobs, and also manage to keeps their lives in perfect order. I think they’re just evidence that androids are living amongst us unnoticed.

I like that my schedule affords me the opportunity to get more life chores done and be more organized than I have been in a while. But it creates a false sense of productivity. Getting a physical is a item to check off the to-do list, but spending three hours at the doctors does not get one closer to her professional goals.

It’s officially been three months since we started working on our own. We decided that even the self-employed should not be immune to the quarterly review, so we took a cold, hard look at our progress so far. And, yes, we did need drinks after.

Overall, we’ve learned a lot, made some measurable progress, didn’t get sick of each other, and had only had two fights. We also missed numerous deadlines, changed focus midway through, and still haven’t figured out how to maximize productivity. In summary, it’s been a moderate success, but we’ve got a long way to go. The most valuable part has been what we learned, though.

Learnings:

• Set a routine. It’s tempting to take advantage of a flexible schedule and easy to fall into college-days habits, like pulling all-nighters to finish projects and sleeping in the next day. However, we found that we were most productive when we established a routine and followed it. You can break from the routine after it’s established, but it takes at least a month to make it stick.
• Don’t always “divide and conquer”. When working with a partner (of any kind) it’s tempting to divide up tasks and work on them separately, but we found that when working on our own we were slower. There is more energy and accountability when we work on tasks together than when working separately. Moving forward, we’re going to try to build in more time when we work together to finish a task.
• Don’t wait for perfection. This is easier said than done. When we started, we said that we were going to operate in the rapid-prototyping mode, and just create content and get a site up. I agree with this concept in theory, but when I’m writing content I’m reluctant to let it go before I’m totally satisfied with it. Which may never happen. I’m trying to learn to let go and just get stuff done.
• Establish smaller, measurable weekly goals. Yes, I’m trying to avoid using SMART goals here, but you get the idea. We began in January with a very lofty project plan that mapped out major milestones over the course of five months. While we did break down the milestones into tasks, it proved to be difficult to work towards far-off goals. Now, we’re trying to focus on short-term tasks (weekly) with less attention to the long-term goals. For example, this week we will create five new web pages with content.
• Have realistic expectations. This has implications all over the place, but since this is about couples working together, I’m going to focus on having realistic expectations of your partner. We made the mistake of overpromising what we could deliver, and then believing each other’s promises, which is really hilarious. You know your partner better than anyone, and you know that he (or she, it definitely goes both ways) is full of shit most of the time. Why would you believe him when he says he’ll put up a website in four hours, or write a whole e-book over the weekend (ok, I did that)? It’s a burden, for sure, to figure out what’s realistic for your partner to achieve, but let’s face it - you know better than he does. If you start to establish realistic expectations of him, and explain why, over time he will start to be better able to do so for himself. (And, yes, the two fights were because of this.)
• Get an accountabilibuddy. Yes, I am stealing that term from South Park, and yes, I’m talking about finding someone to be accountable to. Be honest about what you struggle with the most. Maybe it’s focusing for more than five minutes without checking Facebook, finishing tasks on time, or communicating when you’ve fallen behind. Whatever it is, pick something that you want to work on, and then make yourself accountable to someone. It can be a colleague, a friend, your mom, it doesn’t matter, as long as you check in with that person regularly about how you’re working on your chosen challenge.

A few weeks ago, I stumbled upon a site called Hassle Me, a service that will email a reminder to you at “semi-unpredictable” intervals. I was intrigued by the semi-unpredictable part, because studies in behaviorism suggest that variable ratio (think slot-machines) and variable interval (think pop quizzes) schedules of reinforcement have higher and steadier response rates. And I know that my response to fixed interval reminders (like Outlook meeting reminders, or my alarm clock, for example) tends to worsen over time until I ignore whatever the consistent trigger is.

I wanted to test the service out, but couldn’t think of what I wanted to be reminded to do on a semi-regular basis. Most work-related tasks I either do every day, or am overly aware that I’m not doing them, so an email reminder just seemed to be overkill. Today, however, I was reminded of the one thing we always forget to do as I was re-folding what seemed like 40 brown paper bags - bring our canvas bags to the grocery store. We went through a phase in which we actually bought canvas bags every time we went to the grocery store because we never remembered to bring them, and then we just gave up. We’re at the point now that unless we have a bonfire, we are going to be overrun with paper bags.

I set up a “hassle” for Kris and I to be nagged about canvas bags about every 5 days, which is probably the frequency we go to the grocery store. HassleMe promises to email one of us at random. I’ll keep you posted on how our behavior modification experiment works out.

In a previous post, I attempted to wage a battle between Gen X and Gen Y entrepreneurs, a largely unfounded one it turns out. What I uncovered, though, is that my question had less to do with age and the ambiguous borders of Gen X and Gen Y, but more to do with the value of traditional work experience against new entrepreneurism. It’s essentially a question about the value of experience, which interestingly is at the center of the current presidential primaries, and the subject of March 10th’s Time magazine cover story. So what is the value of experience?

Despite my alt-outlook on most things, I have a soft spot for the old school, and nowhere else as much as when it comes to education. For most of elementary school, I went to Catholic school. The nuns drilled us on our times tables and sentence diagrams, and I attribute any subsequent academic success to that experience. As an educator, I’m into experiential and project-based learning, but think it has little value if the students don’t have the basics mastered. As a teacher in a great inner-city high school, I saw otherwise bright, creative, and insightful students fall short of expectation consistently because they hadn’t mastered basic grammar and vocab. Why is this important? Well, there is a business equivalent to paying your dues and learning the basics. And while I rejected the traditional path of climbing the corporate ladder, I learned from the work experience of doing menial labor, of trying to fit in, of following orders. Even if what I learned is that I hate it.

But does this learning put me at an advantage or disadvantage as my own boss? How do I size up against a teenager with a great idea, energy, and ingenuity? From my perspective, the pros of starting a business, sans experience:

• Thinking out of the box. Wait, it’s more than outside the box. It’s what happens when there is no box. And it’s pretty cool.
• Risk-taking. The younger and less experienced tend to be less risk-averse, which can be an asset in the startup environment.
• Ego. Confidence can take you a lot of places, and youngsters who haven’t experienced rejection and humiliation in the workplace have plenty.
• Energy. Imagine what you could get done if you could still pull all-nighters fueled by hope and Red Bull.

The pros of starting a business after putting in some time in the corporate world:

• Communication skills. Working with people beyond the ones that live in your dorm often makes you practice communicating effectively.
• Knowing how to play the game. Like it or not, there are definitely rules and etiquette in the business world, and knowing them can improve relationships with other businesses.
• Humility. Nothing like sending out dozens of resumes only to be rejected or being ignored in meetings to make you realize no one thinks you are as smart as you do. And that’s not a bad thing.

My thoughts clearly aren’t very decisive; neither was the expert opinion in the Time article. Experience was not a strong indicator of future achievement and success. In the political realm, there are too many new variables for experience to mean much. The same could be true in the startup environment. There are models of success, but no gaurantee that they can be replicated. The author of the article, Von Drehle, says, “To a keen student of human nature, all life offers lessons in how to lead, inspire, and endure.” Indeed, it is all of our experiences, and our ability to learn from them, that can be lessons in how to start a business.

My husband and I are attempting to start our own business just as we are about to hit the big 3-0. So as a late-twenty something in a decade that has seen many entrepreneurs in their teens and early twenties, I feel almost ancient as I begin. I question the value of working in more traditional environments in my twenties, and wonder if the learning experiences provide a long-term competitive edge against the younger entrepreneur, or if I’ve just essentially lost time. With that question as the starting point, I set out to compare the Gen X vs the Gen Y entrepreneur.

As I began researching, this became harder than expected. A big reason is that according to some sources, I technically belong to Gen Y. The boundaries between Gen X and Gen Y are pretty hazy and the starting point ranges from 1976 to 1981. As someone who was born in 1979, I could be in the midst of a major identity crisis right now. But I know who I am. I love Winona Ryder and Jon Cusack movies; I was 12 when Nevermind was released; I wore flannel as a pre-teen; I was pretty apathetic and angsty throughout high school and college; I had a computer when I was five, but I didn’t use email until my study abroad in college. I identify with the Gen X set.

These Gen Yers, or Millennials, get a lot of media attention, and rightfully so. It seems everyday another 19 year old drops out of college after getting millions in VC. With all the creativity and technology acumen, do these Gen Y entrepreneurs have staying power? The experts characterize the Gen Y entrepreneur as:

• The entrepreneurial generation
• Value work/life balance
• Disenchanted with corporate model
• Enjoy taking risks (who doesn’t under 30?)
• Able to leverage technology (they are, afterall, digital natives.)
• Good at teamwork and collaboration
• Want to make a contribution
• Relentlessly optimistic
• Non-stop experimenters
• Confidence, independence, enthusiasm, and impatience

OK, not looking good for Gen Xers. I mean, we’re known for being grungy slackers, for being disloyal and lazy, and worse, apathetic. So what do the experts say about Gen X entrepreneurs? While there are fewer search results, the findings are interesting. Guess what an author said about Gen X in 1998:

• Gen X considered the most entrepreneurial generation
• Disenchanted because of broken homes, downsizing
• Value work/life balance
• Able to leverage technology
• Legacy will be individualism and entrepreneurship
• More collaborative and comfortable with teamwork
• Less hierarchical, wants to be involved in decision-making process
• Self-reliant, candid, rule-shy

Huh. So, besides the cynical vs. optimistic outlook and the tremendous size of Gen Y versus the smaller numbers of Gen Xers, there is virtually no difference between us. Really. So my “faceoff” might be for not? Meredith Bagby said of Gen X, “Whether we like it or not, we’re sort of a transitional generation. We grew up with computers, but we still grew up in a traditional world. What’s interesting about Generation Y is they not only have computers but they also have the Internet. And those who’ve been really immersed in that technology have a completely different way of thinking - it’s more chaotic and random.”

Ok. I’ll take transitional generation, as long as we’re clear that “transitional” means that Gen Y has been riding our coattails, following on the trail that we blazed, except with the addition of their gushing optimism and care for social change. So how does the Gen X collision of technology and tradition stand against the digital natives? Part II talks about tradition, experience, and chaos – should you learn the rules of the game before you break them, or write your own rule book?

There are days when you’re just not feeling it - you’re tired, unfocused, inefficient, bored. In the business world, these days are called Fridays. In an office environment, these Fridays can make any worker feel like a kid on a long car ride: you’re strangely optimistic about what will happen when it ends, but the day seems infinitely long. Instead of spending the whole day saying “are we there yet?”, the worker, in true adult fashion, silently stares at her computer screen and waits for the hours to go by with a burning hope that the boss will suggest heading to happy hour at 4pm.

When you work in a company, there are certain strategies for dealing these “Fridays”. The strategies include: drinking lots of coffee, checking your email every 2 minutes, “catching up” with co-workers you haven’t talked to in a while, and cleaning your desk. But what happens when you work from home? These strategies (with the exception of the coffee one) are not effective, because trying to appear busy to yourself is just insane. So what are the self-employed and the entrepreneurs to do with these mediocre days?

It seems to me that there are 3 options:

1. Tough it out. You can chose to accept your minimal productivity, and ride out the work day anyway. With this approach you may be able to get a few small tasks done, thus getting you closer to your goals. However, it may take you way longer than it otherwise would on a better day to accomplish this. For me, this is the most depressing approach. It does not feel good to finish something in 4 hours when it should have taken 30 minutes. And even if I stare at the computer until 2 am, I know that my output is virtually non-existent, despite computer face time. Toughing it out sucks, but sometimes it must be done.
2. Work on non-critical or non-work-related tasks. This option is the equivalent to the worker bee cleaning her desk. This is when you do laundry, wash the floors, organize your mail, etc. You feel productive because you are still getting things done, albeit while blaring 80s music and not really thinking too much. This approach works if you’re totally delusional, which I am.
3. Cut your losses and head to happy hour. If you aren’t good at sitting around getting nothing done and lying to yourself about it, this step might be for you. If this choice sounds selfish and unproductive, well it is. But that does not make the afternoon Bloody Mary any less sweet (I mean spicy). In the creative process, this would be like your “artist’s date” where you would be “re-filling your well.” So maybe cutting the work week short is lazy, or maybe it’s just the thing you need to energize you.

-Kate Miffitt 

How many times have you told yourself that if you only had a few extra hours in the week that you could start your own business? How many times have you seen money and opportunity squandered at other companies and thought “if I only had a business…”? Well you know what? I wonder if it’s better thought than executed.

Believe me, I am the biggest bitch in the neighborhood and I am also a person who thinks if I had $10 and 4 hours, I could make a million overnight. But bootstrapping (in real life) is a hell-of-a-lot harder than you think it is… and the costs aren’t just financial.

Bootstrapping is defined as “a collection of methods used to minimize the amount of outside debt and equity financing needed from banks and investors”. Having been inside at least three bootstrapping companies (I wouldn’t call all startups bootstrappers), I am pretty aware of the methods used by companies to minimize cost and increase profits.

But let’s turn this thing on its head and think about the real cost of bootstrapping a company with your spouse while you are still trying to maintain a day job (to fund your company).

Fuck finances, I think the real cost of bootstrapping is:

1. The Cost of Time and Life

Not everyone is lucky enough to have a savings account they can dip into or have been given a small startup loan. Some of us out there are working a day job to fund our prospective startup company. Such is the case with my wife and I. And you know what happens? My existing work slips and my lifestyle gets pinched.

I end up pumping out crappy work (which then endangers my “funding”) and I end up working until all hours of the night, not sleeping, eating Doritos like it’s the last substance on earth and never leaving my house for fresh air.

2. Cost of Relationship

After a 40+ hour week with my day job and another 20+ hours on the startup, the only thing you seem to have between yourself and your spouse is the pure language of timelines and economics. There ain’t no honeymooning when you are bootstrapping. You never get loving time and your marriage becomes all business.

In business terms… this is not a sustainable growth pattern.

3. Cost of Social Life

First off, let’s be clear: I never had a social life… or, at least, not how you are thinking. If going out on a Friday night, drinking more than 10 sailors, offending 90% of the people I meet, and eventually passing out on the couch while fighting with my wife is a social life… then I’ve got one. Otherwise, the idea eludes me. Though my point stands; when you never get to go out or you’re always talking about your company, you’re going to quickly find that no one is standing near you and your friends stop calling you for that “after work drink.”

4. Cost of Sanity

Let’s recap: working 7 days a week at about 70 hours, my relationship has become a business utility and I never leave my home because my friends don’t want to hear me talk about my ideas anymore… hmmm. I wouldn’t say that I was ever the “sane” type, but I did always have a grip on reality. And that grip is slipping like the California shores into the Pacific Ocean.

5. Cost of Self-Esteem

This is actually the biggest cost for me. I can deal with having no time to myself; I know that I can find time to repair my relationship; I don’t care about having a social life; and I kind of like the odd things that pop into my head now that I have lost my mind BUT the real problem is my loss of self-esteem. This has been the biggest cost in bootstrapping to date.

I thrive on self-esteem (everyone does) and consider it the element in my life that helps me think of how to build a better mouse trap and keeps me driving. The problem is, as you put more time in, you worry about failure and that worry gets to you quickly. You start to feel like you don’t know as much as you thought when you don’t hit the goals you set for yourself (or when you don’t yet have revenue coming in). I’ve had a lot of success in my life and I am great at pitching my ideas to myself and others… but when I don’t see results (because I don’t have enough time to hit milestones), I start looking in the mirror and asking ifI have been blowing smoke up my ass for the past 7 years. Or maybe everything I achieved was just a fluke.

Anyone can make money – anyone can make a lot of money. Funding your own business from a financial standpoint isn’t tough. You may not have as much money as you want to get things done overnight, but if you are smart enough then you’ll make enough to get yourself to the next jump off.

What will kill your business if you let them are the intangibles. The real cost of bootstrapping are those things that you’ll never put in a financial model or revenue forecast.

- Kris Keimig