The Startup Spouses

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

There are a lot of reasons for entrepreneurs and small businesses to have a blog, but I’ll let the internet marketing and social media experts make the compelling business arguments for it. I have started this blog for more personal reasons that I think can be as beneficial for the entrepreneur.

1. It’s the journey, not the destination. If you’re just starting out and developing a business idea, blogging your experience as you move from planning to development can be invaluable. Often our experiences are colored by the outcomes, so if you have a win you may forget all the steps it took to get there, and if you fail, you may be too dejected to uncover where you made mistakes. Blogging about the daily challenges and decisions you make will give you a history to look over at the end and a place to make better choices from in future ventures.
2. You are not alone. Blogging is one way to form community with people who are working towards similar goals. This is especially useful if you work from home and primarily discuss your ideas with your dog (which I totally do) or the baristas at the coffeeshop you have made your office (which I’m too shy to do).
3. Ideas beget ideas. A funny thing happens when you start working on your own ideas and solutions: you keep coming up with more ideas and solutions. It feels like the synapses in your brain start firing more rapidly when your work for yourself, which is a good thing, but it can also be distracting. A blog can be a bucket or holding place for your brainstorming, so you don’t spend your day chasing ideas and not getting anything done.
4. Sometimes you just need busy work. My biggest pet peeve at every job was the inevitable busy work that was involved. Now that I work from home, I’d happily take on some busy work. Small tasks that don’t take up too much brain power are great to have to get your brain firing and to feel a sense of accomplishment. A blog provides good “busy work” tasks. You can write a post in the morning to get your day started, check out other blogs during lunch, and reply to any comments while watching American Idol. You are still nurturing your business while getting a mini mental break.
5. Learn about yourself and your work style. When you stop comparing yourself to the guy in the next cubicle or worrying about your next manager review and start facing you own strengths and weaknesses as you sit in your apartment by yourself all day,  you can learn a lot. Most of the blog posts that come to mind have to do with observations about myself (like noticing I hadn’t worn a bra in 4 days because I didn’t have to go to an office) than with concrete entrepreneur advice. Regardless of where I am professionally in 6 months, the knowledge I gain about myself and how I work with my partner will be valuable in any future endeavor.

An entrepreneur or small business blog can yield wins for your business, but it will also enhance your personal and professional development.

Most entrepreneurs face  decisions about systems and thinks about how he/she will communicate, track, plan, manage, and budget for his/her company. When is it appropriate to invest the time and potential money into getting “set up”, so to speak? There is no magical formula that I’m aware of (did I mention that I’m not an MBA-type?), but what follows is our experience and some criteria that resulted.

I spent some time upfront, probably due to some deep personality flaw, exploring options for different tools to use to support our efforts. Having had some experience with Microsoft Project, I chose to stay away from such a clunky application. Besides, it has way more functionality than we need. I considered Basecamp, but ultimately that too seemed to be overkill on a small startup project spearheaded by two people. Ultimately, we decided on using Google docs to collect, collaborate on, and track competitive research, meeting notes, designs we like, and any brainstorming. We also use Outlook for its calendar function. I actually use the Mac version of Outlook which is called Entourage, and has a neat little feature called the Project Center. It has very basic project management functionality; you can set up tasks with notes and invite collaborators. The deadlines appear in your Outlook calendar. We decided this was all the project functionality we needed given that we have short-term (four months), manageable milestones, so it worked nicely.

If I had to give advice to others as to what to consider when thinking about systems to use, I would recommend the following criteria:

• Effort. Will implementing a particular system improve efficiency, or will it take you more effort to research, setup, and update than it actually saves? One of my complaints of project management tools has been that I find that updating projects is time-consuming, and I often don’t make use of the plan when actually doing the work, so the effort is not well-spent.

• Peace of Mind. Does having the system in place make you feel more comfortable, confident, even legitimate? Well, then maybe a few hours researching will be well-spent if you can take yourself more seriously afterwards. It’s like getting new workout clothes before starting a new exercise regimen; they aren’t necessary, but can sometimes provide great motivation. Just be aware of how much time you spend trying to feel more like your own boss, rather than actually doing work.

• Scope and Scalability. Depending on the nature of your business, it might make perfect sense to invest a lot of time upfront thinking about systems, either because your business plan is large in scope or because you need to be able to accommodate rapid growth. Both scenarios require good organization and infrastructure to be most successful.

My husband and I are opposites on many fronts, which is a good thing in many cases, and certainly in our business ventures. We tend to balance out each other’s strengths and shortcomings. Kris is definitely the CEO type; he’s creative, inspired, unafraid of failure, interested in throwing ideas out and seeing what sticks. I probably am more the COO type; I am strategic, systematic, organized, and interested in understanding how things work. He’s the idealist; I’m the realist. It’s a nice combination, when in the right balance. What happens when it gets out of whack? Plenty, as it turns out. We’re trying to operate in the rapid prototyping mode; get a product together quickly, get feedback, edit, repeat until satisfied/gazillionaires. But we’ve each managed to create roadblocks to our progress that are just byproducts of our personalities.

It might have sounded flattering when I described Kris above, it was not intended to be. His manic creativity and idea generation is sometimes more of a problem than anything else. For example, just as we were poised to be ready to get a site up on schedule in mid-February, Kris had another idea. A good idea, one that if implemented correctly could at least be a short-term win in a less competitive space. So we dropped everything and have spent two weeks developing this. The inherent problem is that this could go on infinitely, as I have seen in the past with Kris’s ideas. He comes up with an idea, is quick to start implementing, and promptly abandons it when the next idea comes along. I am only lucky that he does not do this with wives. Will the idea-chasing ever pay off? Not without some serious follow through somewhere.

I have certainly created some bumps along the way myself. Because I am so concerned with how things work, I often think more about the process than the product. And because I’m a long-term thinker, I’m not a great short-term doer. Bummer, because I’m currently the main resource in developing our product. To date, I have created a few delays. The first was that I didn’t feel comfortable contacting vendors without an @domain.com email. Nevermind that we don’t have a website or anything yet. So I delayed a task for three days because I didn’t have the “right” email address. Absurd. I also agonized for days over what systems we would use for communicating, tracking, planning, and project management. I mean, we are a married couple who live and work in the same small space, and I’m obsessing over setting up my Outlook calendar and deciding whether we should use Basecamp, or if Google docs is sufficient. Systems thinking is useful when you actually have something to organize, but apparently a handicap when you have no content.

So we’re still experimenting and trying to find the best way to make use of our respective skills. We have a lot of potential as business partners, but we both need to stop looking at our different big pictures and start working already.