A Tale of Two Jasons

It was the best of times, it was the worst of times
We were all going to have great exists, we were all going direct the other way

A few months ago, Jason, a founder of one of our portfolio companies, reached out to me about some challenges his startup was facing. As it happened, I was running late for my flight from Houston to Istanbul, so I had to cut short my Zoom call with Jason.

Istanbul and The Clashing Rocks

After enduring a long flight and getting a good night's sleep, I found myself wandering the enchanting city of Istanbul, which gracefully straddles both Europe and Asia. As I strolled along the western bank of the Bosphorus Strait, captivated by the narrow waterway connecting the Black Sea and the Mediterranean, I couldn't help but feel a pang of guilt for having cut short my conversation with Jason back home in Texas while he needed me the most.

Bosphorus Strait in Istanbul, the Clashing Rocks reside on the West Bank of the strait. The author took this picture in February 2023.

It was then, that a sudden realization struck me: millennia ago, right where I stood, an ancient Greek hero, also named Jason, had once faced his most formidable challenge as he navigated the Bosphorus in pursuit of the fabled Golden Fleece. At the very spot I was standing, Jason encountered the treacherous Clashing Rocks, or the Symplegades — a pair of rocks that threatened to crush any vessel daring to pass through.

I'm here to recount one Jason's story to another. Though separated by millennia, these two Jasons can find their stories intertwined, bound by a common motif as they each set sail on their respective adventures.

Jason, a Bootstrapper with a Vision, on a Mission

Jason and the Argonauts’ Quest to find the Golden Fleece
Image created by the Author using Midjourney

Jason, the mythical Greek hero and rightful heir to the throne of Iolcus, was famously known for wearing just one sandal (literally bootstrapping it!) in his early years. To reclaim his throne from the usurper, he embarked on an epic journey to search for the elusive Golden Fleece. This quest led him to the edge of the known world (in the modern-day Black Sea), and he eventually faced treacherous challenges when passing through the Clashing Rocks at the Bosphorus Strait, where I was standing.

The first lesson our modern tech founder, Jason, can draw from his ancient namesake hero is the power of vision. Our Greek hero knew his destiny and purpose, and he was a man with a clear vision, on a mission. In his subsequent sea voyage, as the captain of the Argo ship, Jason passed his vision and mission to his crew and inspired them toward a common objective. He exhibited foresight, fortitude, and unwavering determination, motivating his crew to boldly pursue their mission.

Argo, the Product

Jason's remarkable sea voyage began not at the sea, but in the forest, where he searched for the finest wood to build the most magnificent vessel of the time. Wanting a ship with fifty oars, and strong enough to endure the long and arduous voyage, Jason enlisted the best shipbuilder of the time, Argus, to design the vessel.

Argus designed and constructed a ship with a sturdy hull, a streamlined shape for speed, and the resilience to withstand the harshest conditions. The ship was further enhanced by incorporating divine Dodona oak timber into its prow, granting it the power of speech and prophecy. Jason was so pleased with the ship that he named it The Argo in honor of the shipbuilder Argus.

Argus designed and built the legendary Argo ship.
Image created by the Author using Midjourney

Similarly, the modern-day Jason can draw parallels from the ancient hero's foresight to build an exceptional product. Just like the Greek hero did not rush to the sea with a boat built by a random person, modern-day Jason needs to carefully identify a software architect (Argus) with the skill set to design and implement sound architectural frameworks. It's essential to ensure the product is designed to last and built to serve its intended purpose (the vessel must be fit for the journey).

After the release of Argo 1.0, the development and maintenance team (Argonauts) should persistently refine the product by adding new features and making it more durable as the waves become higher and the wind changes direction (as user demands increase and market shifts occur). By doing so, the contemporary tech founder can also create a product as strong as the Argo.

Argonauts, The Management Team

Mythical Jason and Argonauts (his management team).
Image created by the Author using Midjourney

With the magnificent ship Argo ready to set sail, Captain Jason recognized the significance of assembling a diverse crew of exceptional individuals, each possessing unique talents and skills. This group, later known as the Argonauts, was thoughtfully selected, with Jason inviting renowned heroes and skilled craftsmen from various Greek city-states. By meticulously bringing together a crew that combined their distinct abilities and expertise, and fostering a cohesive unit, Jason ensured the success of their epic adventure.

The modern-day Jason can learn from the Greek hero the importance of building a strong management team. Like the Argonauts, the management team should complement each other and work as a cohesive unit. Modern-day Jason must foster a collaborative and supportive environment within his company, and encourage the team to solve problems together and grow together.

Resilience, Perseverance & Seeking Advice

During the epic quest, Jason displayed remarkable resilience and perseverance, refusing to give up in the face of adversity. On numerous occasions, he sought guidance from Athena. Without the wise King Phineus' advice, Jason wouldn’t have known how to navigate the Clashing Rocks. The Greek hero demonstrated humility in seeking counsel from both gods and sages.

In the world of entrepreneurship, modern-day Jason will undoubtedly face a plethora of obstacles, including technological challenges and customer acquisition. To overcome these challenges, Jason must remain steadfast and stay the course while also demonstrating humility by seeking advice from experienced advisors or venture partners (in case of Greek gods or Oracles aren’t available).

Data-Driven Decision-Making and Strategies

Jason released a dove to fly between the Clashing Rocks
Image created by the Author using Midjourney

Among all the perils Jason and his crew faced, none were as daunting as the Clashing Rocks. These treacherous rocks moved together and apart, crushing anything that dared to pass between them.

Seeking a way to navigate the dangerous passage, Jason devised a plan. He released a dove to fly between the deadly rocks; the dove barely made it through, losing only a few tail feathers as the rocks closed in. With careful observation, Jason understood the rhythm of the Clashing Rocks by collecting critical data.

Under Jason's command, the crew rowed with all their might, approaching the rocks at the exact right moment, the Argo narrowly escaped the deadly grasp of the rocks. Jason and the Argonauts triumphed over the Clashing Rocks through accurate data-driven decision-making, strategy, and execution.

Two Jasons, One Journey

Isaac Shi at the Golden Section office

Jason and the Argonauts continued on their voyage into the Black Sea, in the end, after trials and tribulations, Jason found the Golden Fleece in Colchis, reclaimed his throne, and ultimately earned his place in the pantheon of ancient Greek heroes.

Eureka! Our two Jasons, separated by vast stretches of time and circumstance, find a shared connection in their adventurous pursuits. By embracing the enduring lessons of leadership, wisdom, and resilience, our contemporary tech founder can follow the ancient hero's footsteps, traversing the treacherous seas of entrepreneurship and ultimately attaining his own version of the Golden Fleece.

Meanwhile, I can take solace in the knowledge that I have offered my fellow entrepreneur Jason the best guidance I can provide.

By Isaac Shi
March 30, 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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