Categorized | Shoestring Startup

Two Entrepreneurs, One Bedroom.

Two Entrepreneurs, One Bedroom.Husband and wife entrepreneur teams do two things exceedingly well: succeed or fail. Two entrepreneurs in one house can cause big problems for both the business and the relationship. Luckily, in the midst of stressful challenges, my husband and I learned the greatest lesson of all: divide and conquer.

For me, my entrepreneurial journey has been a path lined with lessons. Lessons you aren’t taught in school or at your corporate job. Lessons only discovered by trying something that very few ever do: bootstrapping a startup.

As with all entrepreneurial stories, ours started with an idea; well, in our case, a plethora of ideas. That was the first lesson I learned early on: choose one idea and go with it. How does the proverb go? If you chase two rabbits, you will lose both. And in a sentence, that’s how the first year went. I am an idea maker, but my husband, Jon, is the rainmaker. I’m great at coming up with ideas, but execution is where Jon excels. Every idea I came up with I wanted to see come to life. It was akin to a cerebral Sophie’s choice. Every idea I conceived was like my child and I couldn’t sort the promising ideas from the ideas I should have probably only told my mom about.

Obviously, we couldn’t execute every idea and I was becoming impatient because nothing was catching. That’s second lesson I learned: things take time. Stories such as Facebook are anomalies. When you hear success stories, you don’t hear about the decade of work they put in with no avail, you only hear about when they struck it big.

Divide and conquer

We were at each other’s throats. Business was bleeding into our personal lives and though it’s extraordinarily difficult to continually cauterize, it was vital for us to keep business out of the home. Dividing the work was our solution: we chose two ideas, Jon took one and I took the other.

I thought choosing the ideas to pursue would be difficult, but it was rather simple. We chose projects we were passionate about and could execute ourselves. I chose to pursue a natural passion for any woman, fashion. Jon took on a patient-oriented health web application.

Boot Buddie is a fashion accessory that keeps pants in place while putting on and wearing boots. I came up with the idea when I became frustrated at my jeans constantly scrunching at the knees as my jeans rode up in my boots. Boot Buddie wraps around your jeans at your ankle and holds your pants in place. Boot Buddie gives you a polished finish when tucking pants into boots. I believe in my product. It works and it solves a problem I’ve had dozens of friends complain about. For more information, visit

Two Entrepreneurs, One BedroomHealth History Software is a smartphone application that allows patients to quickly and securely access their health history on the spot. Your smartphone will soon be able to tell you if you took your medication this morning, the address and phone number of your primary care doctor, when you got your last tetanus shot and much more. For more information, visit

Lessons in execution

As Jon began building Health History Software, I began making the plan for Boot Buddie. The most fascinating aspect of bootstrapping a startup is the different roles you play at any one time. You become more than an entrepreneur, you become what’s needed. You are an inventor, an accountant, a lawyer, a marketer, a designer, a salesperson — the list is endless.

I made the design for Boot Buddie and sent it to friends and family for testing and feedback. The response was phenomenal. It worked, it solved the problem they had dealt with for years. The only previous solution was shoving your pants in your socks which is not exactly comfortable and definitely stretches out your socks. I was thrilled that my idea was becoming a reality. Next up was setting up the website and marketing.

There were several decisions to make while approaching how best to develop After loads of research, I chose Volusion for the website because of it’s balance of value and price (we’re bootstrapping after all). I had previously designed and coded my own websites but I was impressed with the professional look of Volusion’s templates and I had the site up in less than a week. Additionally, we use PayPal for payment processing.

Marketing is a lot like baking a cake without a recipe. The first dozen cakes are probably going to taste like wet, brown flour, but then you accidentally add that secret ingredient and WHAM! it’s the best cake you’ve ever tasted. Marketing is nearly all guess and check. There are general principles, but everyone has a different strategy and unique products need unique marketing.

In my experience, online advertising is not for the bootstrapping entrepreneur. It may work fabulously for established brands or products with money to spend upfront, but guerilla marketing has given me much more success. I went back to the basics. I sent samples to reporters and bloggers. I requested their feedback and genuinely did not expect a good review, article or blogpost. I’ve always felt that transparency is the best approach. I think pushing bloggers or reporters to do what you want, when you want is a great way to burn a relationship, get a bad review or get no review at all. Additionally, I researched shoe stores, learned about their market and approached the owners individually to see if Boot Buddie would be a good fit for their store. Establishing long-lasting relationships is well worth the effort at the beginning. It’s a slow process, but in the end it is very rewarding.

Health History Software launches in January 2012. In preparation for our launch next year, the first 500 visitors to sign up at will receive a full year of the service free. Health History Software will provide you the medical information you need, securely and when you need it.

If a retiree needs to make sure he’s taken all his medication at breakfast, he can just check off his pills on his iPhone. If a patient gets to the dentist and forgot the name and address of her primary care doctor, it’s there on her BlackBerry. If a mom takes her son to a new pediatrician and forgot if he had received a booster shot, she can quickly check on her Android. It’s that easy — information you need, when you need it, delivered to you securely.

The challenging part of building a smartphone and web application is the upfront investment. It takes a lot of time and work to code the backend software for the website and application. We take security very seriously and believe that no one should have access to your medical data except for you. Jon is creating an application that absolutely protects your privacy. The investment has been well worth it and we’re thrilled to launch Health History Software in a few months.

Losing friends, gaining partners

The last lesson I learned was this: not everyone gets what you’re doing and not everyone believes in you. Many of my friends didn’t like my ideas and didn’t understand what I was doing. It hurt me at my core and it wounded my self-confidence in my business. I pushed through it and gave no weight to their words. I learned to believe in myself and to not depend on the approval of others. The funny thing was the more I believed in myself, the more they believed in me. The average person would never dream of doing what we do. The average person doesn’t understand the amount of blood, sweat and tears it takes to get a business off the ground. So stop only talking to average people. Find the entrepreneurs in your life. They’re there, believe me. They may not be currently bootstrapping, but they have ideas and they have dreams. Those people are the ones that will give you legitimate feedback and will encourage you through the rough patches.

Nothing is quite like bootstrapping a startup. It’s challenges are unique and difficult, but an entrepreneur’s life contains more opportunities, more value and more freedom than a corporate job ever will. Besides, who wants to be average anyway?

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