Curiosity, Courage, and Cowboy Songs: My Entrepreneurial Journey

Photo by Priscila Duprees

I’m 45 years old. My first entrepreneurial venture probably started 40 years ago with a lemonade stand. A wonderful cliché from the eighties, where a kid could test product adoption right from the sidewalk with their neighbors, although the results weren’t always clear, especially considering that special customer called mom, who would save the day by buying more than just one cup.

At age 9, I was already working half days in my grandfather’s factory during summer. (He never paid me. There goes your first lesson boy) At 15, I imported and sold electric guitars and sheet music at school. By 17, I had started DJing at family events. I won't go further into the dozens of ventures I've had up to now, only to establish that at some point I thought anyone could be entrepreneurial and creative. But the truth is, you’re born with it.

I think there are many factors that shape how we see the world. For me, it's partly about legacy. And I don’t even have children. But I'd like to know I've contributed to making the world a bit better once I'm gone. To have left something behind… my music as an expression, preserved on digital platforms. The instruments I build, passing between generations of artists who continue to play our story. My business books, to help others navigate a hard, difficult, and uncertain path. Maybe an innovation that creates new jobs. I've never felt comfortable thinking only about securing my own future without considering others. I've always been a dreamer, perhaps a bit insecure and egocentric traits common among overachievers. But how satisfying it is to see a product on a supermarket shelf or in national distribution and know you created it from start to finish.

Dreamers and the curious often struggle to adapt to most organizations. We aren’t made to come in and perform mechanical tasks following a manual from A to Z. We need to ask ourselves how we can do it better, more efficiently. How can we unlock the full potential of the entire system, creating strategies no one requested? Not driven by productivity alone, but because our obsession simply can’t be contained, often making those around us uncomfortable.

Most of the time, we get congratulations, recognition, followed by a "it’s not you, it’s me," and a pat on the back as we say goodbye.

At some point in life, you'll realize you want to be an entrepreneur. Ninety percent of people prefer fixed work hours followed by Netflix. Those who don’t must know the path resembles a country song full of broken hearts, long dusty roads, and occasional shootouts.

You need to know there are no fixed schedules, that the journey is often lonely, dealing with the state and its regulations, banks, cash flows, logistics, operations, marketing, and sales, not to mention cleaning, catering, and delivery.

You must know that you aren’t doing it merely to captain your ship, to be the cowboy in that country song, to become the first millionaire in your family, or to make your parents proud. We do it because we are different; we identify, build, develop, and involve others to foster life and growth before embarking on our next adventure.

You must know conditions are tough, forcing you to be a solopreneur and learn how to handle everything yourself initially. At first, it’s intoxicating for a curious mind with so much to absorb. Later, you learn to play each position, wearing the appropriate hat for each role. You must know when to disconnect from loving your product to become objective. Eventually, you discover the best outcomes occur when you make things happen alongside others who are better and smarter than you in their respective fields.

Ultimately, you become the conductor of the orchestra. You’ve endured sleepless nights, practiced tirelessly, understood the role of every instrument you direct, and it's this unified, organized effort, the tip of the iceberg, that results from a life of sacrifices.

For me, this path must be followed to feel alive and fully leverage our time on Earth, having drunk from every fountain that quenched my curiosity with knowledge and experiences, and building connections at every port I reached, always the new kid in school.

If you’re thinking about starting a startup, don't do it solely for money; generally, it won’t be a quick path. Do it because you're different, because you identify with this story. And if that's the case, don’t hesitate to message me.

Learn, make mistakes, find balance in everything, seek a mentor, and surround yourself with people like you. At home, I wish you the good fortune of having people who love and support you. For everything else, good luck and enjoy the ride.

Article by Gameplan’s Founder Martin Endara Crespo