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A Life of Failure and Gratitude Isn't So Bad After All

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A long time ago, in a desert far, far away, I got an MBA from the University of New Mexico.  It was a night-school thing, and three nights a week, I would go from being an Air Force officer to being a student and learning what the "real" world was all about.  I also played hockey for the school team and was part of a record-breaking 31-game-losing streak, but that's a whole other story. It was during the time of the dot-com boom, and everyone was excited about this new technology the "Internet" could bring.  Everyone was dumping money into the most ridiculous of business models, and I wanted in the game.

I remember those days well.  I met the man who would become my business partner in my next two companies through one of the teaching assistants in my MBA program.  He had an idea to build a website selling original art online,  I had just started learning about programming, and "slightly overstated" my abilities because I wanted to be a part of something that I had built.  Scrambling to recover from overpromising, I went to a local bookstore and picked up a book titled "Teach Yourself CGI Programming in a Week" and started cramming.

The idea behind JustOriginals made sense.  Create a site where people can find the art they want, and they will buy it.  Art is a fragmented market, with galleries taking big commissions, and if we could build something to bypass that, artists should win.  Connecting artists directly to the consumer meant core efficiency and worldwide distribution—what could go wrong?

You'd think that working so hard to help artists would have built some positive relationships.  My first taste of building a business venture was fraught with politics and drama.  It turns out a lot of artists that we found were very contentious regarding the other artists that would be listed on the website.  It made for challenges unlike anything I was prepared to handle.  As I learned more about the art market as a whole, I found it became more and more complex.  Sometimes it is much more difficult to understand people than software.

In the end, the concept failed.  No one wanted to invest in the company, and no one wanted to buy art through the website.  I could blame the artists, I could blame not having enough startup capital, I could blame the business model (people prefer to buy original art because of the emotional connection and you don't get that from a computer screen), but ultimately, it doesn't matter.  The business never made it.  We lost. 

It was humbling to work so hard at something that no one wanted.  But like all failures, we each have a choice in how we deal with them.  Of course I felt low - thousands of hours had gone into that business.  I wasn't a good programmer, I wasn't a good businessperson, I was a failure.  Except that the idea of failing and being a failure is not a permanent state of being.  Failing is how we learn.  It tooks me months to come to that realization, but when it sank in, I realized I was stronger than I had ever been.

So I graduated with my degree, separated from the Air Force, and moved to San Diego.  I started over, this time better prepared and with a much more customer-focused eye on what we were building.

My next venture, with the same business partner, fared better.  Using the lessons we learned, we built one of the first email marketing service providers, CoolerEmail.  CoolerEmail was one of the first strictly permission-based platforms that helped businesses build, send, and track email newsletters.  

Even with the experience of our first failure, getting that started wasn't easy.  I was living in a little apartment, surviving off of part-time programming jobs, and eating a lot of microwaved food, Top Ramen, and mac and cheese.  It took a few years until that company got off the ground and I could devote 100% of my time to it.  After 14 years, the business has gone through some changes.  The new company, GreenRope, is strong, growing, and fueled by 18 passionate people who believe they can make a difference in how businesses operate and grow.  The honor of making the Inc 500 list this year gave a great sense of vindication for all the failures and hard work.

In all, there were many ups and downs, but each provided a lesson.  I am grateful for my previous failures because they are a driving force in GreenRope’s success.  There is no easy path to entrepreneurship.  No one starts a business because they want an easy, stress-free life.

There is very little you can do to prepare yourself for the rigors of starting a business.  I thought getting a business degree would help, and it definitely was a good start.  But so much of business is learned by doing, and seeing others succeed and fail around you firsthand.

The final course of my MBA program was all about applying the principles of Sun Tzu's "The Art of War" to business.  I highly recommend reading it to anyone in business because the parallels are obvious and the lessons are directly applicable to reality.  There are many similarities between war and business, especially in a free market.  Finding and nurturing allies, identifying vendors and managing limited resources are all part of the "game" of business and battle.

Gratitude has carried me through years of long nights, stress about finances, worries of the future, and self-doubt.  The lessons that I have learned from failure have given me the wisdom to know that there are no insurmountable barriers.  There are always threats to every business, but it's how we approach those threats, how we deal with the successes and failures, that make us who we are.

I have failed in business, I have failed in personal relationships, I have failed in software I have written (hate bugs!), I have made the wrong decisions in what and who to invest in, and I'm pretty sure I will do all of those things again.  Hopefully not in exactly the same way, but I know that if I carry the lessons from those failures with gratitude, rather than holding on to the failures themselves, every day I, and the people around me, will grow stronger.

None of us are an island.  We share the effects of those failures with each other, just as we share our successes.  Hopefully we share the lessons, too.  I hope these stories of my struggles in some way provide solace if you are struggling, too.  GreenRope and the people here have built this company from the ground up, without a rich bank or investor, with only ourselves to rely on.  We know what it means to struggle, and we are here with and for you.

Thank you for sharing your island with me.  I hope we can help you build your business, help you run more efficiently, grow and thrive.  From someone who has been there, know that all of us are here to lend the hand that can make the difference.

Until next time,


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