Entrepreneurial Spirit Enthusiasm

The Entrepreneurial Spirit Is One Of Belief

Being an Entrepreneur requires optimism, outsize amounts of it. And many times, there is very little evidence around us to be optimistic. In fact, quite the opposite may be true.

I’ve been called an optimist, but not in a good way. Ironic, given that my ability to point out potential failures –in systems, processes, strategies, code, etc.– has led some to label me a pessimistic party pooper at times.

To be fair, I have had my fair share of setbacks and failures. So I understand it gets annoying to hear me talk with enthusiasm about “my new venture”. The thinking must be I’m setting myself up for disappointment. This can be downright emotionally draining for all parties involved. Specially with a record like this:


I did not finish college

A longstanding disagreement with my father left me unable to pay for school, and deep in debt. Failure.

Leaving Puerto Rico

I struggled through the recession of the 90’s in Puerto Rico with several entrepreneurial pursuits until I built a sign business. Business was good for a few years. After losing some tax breaks for mainland corporations, the Puerto Rican economy started to tighten.

When vendors started going after my clients, I decided to move to the mainland U.S.A. and start again. Maybe more of a setback than a failure, but uprooting a life from the place one is born and leaving family and friends sure felt like a failure.


I started at the bottom of the ladder at a sign company in Florida. Within a year I was promoted to manager of the graphics department. But I wasn’t happy where I lived. The September 11, 2001 attacks made me ponder about a life lived like that. That was when I visited, loved, found a job at, and decided to move to Austin, Texas. Quitting a management position at the company sure was perceived as a failure.

I started in the back room at a print shop in Austin. There, I had very little control over my time, contribution, and possibilities for promotion or career development (I distinctly recall the boss proclaiming how happy she was they’d found me; “The department is now complete” she said). This was unacceptable. I had failed at a smooth transition.

And so I looked for, and found, a job in the local sign industry, where I had a lot more opportunity. Eventually I moved to a second, more successful company. This led to an opportunity in the design field. I quit the sign industry to join a successful environmental graphic design studio. Finally, I had reached the career most designers go to school for.

The Grand Recession hit right about that time. I survived three rounds of layoffs and worked as hard as ever. The recession, combined with the ongoing paradigm shifts in creative work, led to my layoff on January 2010.

That hurt like a failure.


For the years previous to that moment, I had started a small company designing and creating cycling apparel. Up until then, this little enterprise had been mostly a creative outlet. I seized the opportunity of my layoff to build the business while freelancing design services.

The retail nature of the cycling apparel business proved to be a little too much. I lacked the means of production. This meant that every good effort on my part to do right for my clients fell in the hands of mediocre vendors. It also hurt my reputation with the very people I enjoyed the sport with. Eventually, I stopped doing this business. Failure. (I keep the brand, occasionally designing and selling cool bike shirts at Chronic Cycling ).

The cycling business is how I built my expertise in all things online marketing: strong website content, user experience, PPC, SEO (these were the very early days of social). I combined all this with my design background and WordPress website design and development skills, but freelancing was barely a means to make a humble living. Maybe not a failure, but certainly not a success.

So I created a business model for my services that would produce recurring revenue. When a potential partner showed up talking big numbers, I thought this was it, the Big Opportunity.

I have documented some of the downfall of that business relationship on this blog. From back when I was trying to find the courage to move on, making peace with starting over, even doubting myself. I left out the deep depression of several months.

Worst. Failure. Ever.


A lot of these are easier to identify in hindsight, or course. But I don’t let that diminish their importance:

Leaving Puerto Rico and starting over

That was the right call. The economy has now been on a downward trend for two decades, with the last few years a veritable free-fall most economists see no immediate hope for. What that has done is reduce the middle class at an alarming rate and blown up income disparity. It would have been (and still is) incredibly difficult to build a career in a depressed economy. Leaving was one of the toughest choices of my life and one of the most important wins.

My Career Path

As tough as it has been, my unique career path has endowed me with enough expertise to start fairly complex businesses on my own, and know who and when to hire. I offer my clients consulting on:

  • Business Models
  • Process Optimization and Management
  • Pricing
  • Identity and Design
  • User Interface and Experience
  • WordPress Website Design and Development
  • Marketing Strategy
  • Marketing Tactics, including Content Marketing, Social Media, Email marketing, Pay-per-click, Search Engine Optimization, Online Video, and Conversion Optimization

This wide and deep expertise helps me every day. It allows me to help small business, and gives me the confidence I need, specially on the difficult days, to figure out what I don’t know, and also know when to ask for help.

That Last Business

Yes, ultimately the partnership failed, and my decision to leave hurt our initial core team. But we’re all now better off for it. The truth is I did succeed at all these:

  • Create an innovative, all-inclusive subscription business model for online marketing, and demonstrate it viable.
  • Created an attractive business identity and branding.
  • Built a successful business technology stack.
  • Identified our workflows and created a service management system and tools. (along with the original core team of three, we used it to successfully manage what at one time were more than 400 ongoing deliverables for our clients.)
  • I created all clients’ strategy, information architecture for their websites, and creative direction for our team.

I did all this in spite of an unproductive partnership, the equivalent of dragging an anchor. Doing that and building a business to almost $250k in less than two years is a win in my book.

Did it almost crush me? Yes, but I came out of it with a bang.


entrepreneurial spirit enthusiasm

How did I do it? How does anyone take the continuous beating for decades and keep going?

I’m no hero, and certainly they’ve been many, far greater stories of perseverance and triumph. But I suspect this story, my story, is the most common one. Pedestrian, blue-collar, we keep fighting because we believe we can win.

The Entrepreneur has to believe.

I wouldn’t have started a sign company if I didn’t believe I could succeed. I couldn’t have uprooted my life without believing I could do better wherever I landed. I wouldn’t have left the small success I had in Florida if I didn’t think it would be better in Texas. And none of the rest of it would have happened if I didn’t think there was something better on the other side.

This continuous entrepreneurial spirit is enthusiasm driven by belief.

There is no other way to start any venture, change in career, or product, but the conviction it will work.

If this belief seems crazy to others, it seems downright deranged that anyone would go down this path thinking “maybe it won’t work”.

Belief is what drives enthusiasm, and enthusiasm is the Entrepreneurial Spirit.

Sure, the catacombs of business are full with the stories of entrepreneurs who slipped into obsession and excess. But I’m not advocating in favor of senseless pursuits. Good business is sustainable, profitable.

Optimism need not be not stupid.


Success is going from failure to failure with no loss of enthusiasm”
— Winston Churchill

Do the numbers. Survey focus groups. Build the systems. Do your bookkeeping. Run a business professionally. All these, and then some, are essential business practices.

But right now there is someone out there who’s done all of it and failed. It may be you. The only thing that will get you back on your feet is Belief.

Believe. Keep the enthusiasm. Do it. Succeed.

Have a great day,

Nando Journeyman