The Quixotic Quest of Building a Tech Startup

The Don Quixote Bookends at Golden Section’s Houston office

In Golden Section’s Houston office, a pair of Don Quixote bookends adorns the shelf. I purchased these a few years ago not only to organize some paperbacks but as a reminder that the journey of entrepreneurship is never a breeze, and may even invite laughter from time to time. It's essential not to take oneself too seriously, and maintaining a healthy dose of "delusional" idealism and chivalry, as exemplified by Don Quixote, is liberating.

If Miguel de Cervantes were to write your entrepreneurial story, it could be summarized like this…

In a co-working space not so far away, there exists a peculiar breed of individual, the tech entrepreneur. Much like the determined Don Quixote of La Mancha, these visionaries are driven by a blend of idealism and ambition, setting forth on a quixotic quest to build their very own tech startups. Often fueled by the tales of valiant successes like Apple or Google, they set out, just as Quixote was inspired by the chivalric romances, to build their own technology empire. But the path to Silicon Valley glory is paved with windmills to tilt at, and the journey is as unpredictable as it is exhilarating.

Don Quixote used a Barber’s Basin as his Helmet

Just as Don Quixote donned his makeshift armor and declared himself a knight-errant, instead of the Barber's basin, the aspiring tech founder outfits themselves with a well-worn hoodie, Rocinante is his beloved Macbook, but no knight-errant is complete without their faithful squire, his ever-complimentary co-founder. Just as Sancho Panza provided a more grounded perspective to Don Quixote's idealism, the co-founder complements the visionary founder with their own unique skill set, be it technical prowess or business acumen. Together, they form a formidable duo, ready to charge into the edge of the tech world.

Valor, Virtue, and Valuation

But as Don Quixote soon discovered, his path was filled with foes and challenges. For the tech entrepreneur, these come in the form of building the MVP, much like winning a jousting match with a limited budget for lance and armor, he must prove his valor; acquiring customers, much like winning the heart of Dulcinea del Toboso, he must prove his virtue. The elusive "Series A" funding round the Duke and Duchess can provide, for whom he must prove his valuation. Sometimes, the greatest challenge is not external, but rather his own mind.

Don Quixote tilted at the windmills.
Image created by the Author using Midjourney

Yet, the tales of both Quixote and the tech entrepreneur are not solely about battling lions and windmills. They are also stories of camaraderie and personal growth. Just as Don Quixote and Sancho Panza forged a bond through their many adventures, tech founders build lasting relationships with their employees, mentors, and investors. In the face of adversity, they learn the value of resilience, adaptability, and humility.

In the end, the story of the tech entrepreneur often mirrors the arc of Cervantes' classic novel. While many startups, like the dreams of the deluded knight, ultimately meet a sobering reality, there are others that defy the odds and secure a place in the annals of tech history. Success or failure, the tale of building a tech startup is an exercise in human ingenuity and perseverance, a testament to the power of dreams and the potential for greatness that lies within each of us.

So, courageous founders, draw inspiration from the valiant knight of La Mancha. Embrace your inner knight's yearning for adventure. By pursuing the impossible, we reveal the possible, and by embarking on a winding journey, we ultimately discover our true selves, possibly, become the stuff of legends (or the stuff of bookends).

By Isaac Shi
March 26, 2023

Isaac Shi

About The Author: Isaac Shi (born 史宁) is a General Partner at Golden Section, a Houston-based venture capital firm specializing in B2B SaaS investments. As a technically-minded investor, Mr. Shi plays a pivotal role in identifying and nurturing innovative, high-growth startups in the B2B SaaS sector, guiding them to scale their businesses and achieve enduring success.

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Saturday Tech Night: CTO Christopher Walken at Golden Section Studios