Red Dead Redemption 2 and Failing Startups

Recently I had a lot of fun playing Red Dead Redemption 2. Released in 2019, it’s a game acclaimed by gamers and critics alike, and I wholeheartedly agree with their opinions. While I can write several posts about what’s great about the game, I’d like to discuss the strange similarities I noticed between its plot and my decade-long experience in the startup world. Beware that this post contains significant spoilers over the entire plot of the game - so proceed with caution!

Set in late 19th century fictional America, the game follows the fate of the Van der Linde gang. Led by the eponymous leader Dutch van der Linde, the outlaw gang consists of about twenty members, including the protagonist Arthur Morgan. The game begins with the gang barely escaping a disasterous ferry robbery, hiding the large amount of money they had robbed somewhere in the city and leaving it behind. The gang has a clear goal: escape, survive, rebuild, and reclaim the money. Unfortunately, their attempts to regain footings keep failing and drive them even deeper into the mires. They keep losing members and narrowly escaping one disaster after another, eventually leading to the implosion of the gang at the end of the game.

I first noticed that Dutch reminded me of some startup founders. Then I also realized that other characters bore some similarities to others I’ve known in the industry. In this post I’ll write about a few characters and how they can fit into both a 19th century outlaw gang and a 21st century startup.

Dutch - Leader of the gang / visionary founder

Dutch is a visionary with a silver tongue. He has successfully led the gang for over two decades, overcoming setbacks and continuing to grow. Under his codes of conduct, the gang functioned more like a pseudo-family than a group of self-interested individuals. Despite the gang’s low morale at the start of the game, they still respect him as their leader. He leads the gang to a new hiding place where they can recover and seek new opportunities.

Unfortunately, his plans keep failing. The train robbery, albeit profitable, sets a powerful, vindictive businessman on their tail. In the south, his attempt to pit two rival families against each other for profit backfires, leaving him outwitted. The bank robbery in a large city ends disastrously, resuling in the death of several members and the loss of their hard-earned money in a shipwreck. He keeps on taking even riskier gambles in desperation, even instigating a Native American uprising.

As he keeps getting more and more stressed and cornered, he starts to unravel. Despite having no clear plan to get the gang out of trouble, he insists that he does. When faced with criticism, he perceives it as personal betrayal and demands obedience. He begins to betray his own codes of conduct, such as not killing innocents or always rescuing the gang members, whenever it suits him. Ultimately, he loses everything but his life: his virtues, his gang, and his family.

With his grand vision, lofty values, oratory skills, and competencies, Dutch reminded me of startup founders at their best. Likewise, his fall from grace under constant pressure and setbacks also reminded me of how they fell apart as individuals along with their businesses. It was eerily familiar to me: their desperation as they saw no path forward; the false hope they fed the employees and themselves; and their dismissal of any critic as a traitor.

It made the already tragic plot doubly harrowing for me, as it reminded me of my own experiences with failing startups. Nevertheless, it also made me more sympathetic toward Dutch than many other gamers who seemed to mock his failure without second thought. Having watched great, respected founders break under pressure, and being unsure whether I could have overcome such pressure had I been in their place, I couldn’t simply attribute Dutch’s fall to his personal weaknesses.

Hosea - Level-headed lieutenant / reliable Chief Operations Officer

A decade older and more experienced than Dutch, Hosea serves as the gang’s voice of reason. He favors more peaceful methods for making money, reducing their visibility. He is also realistic about risk and reward, counterbalancing the more ambitious and optimistic Dutch. He is the first to notice Dutch’s increasing recklessness and tries to steer him right. Hosea fears the gang will suffer for its recklessness, a fear that proves accurate. His death during the bank robbery precipitates the gang’s downfall. Without Hosea’s counsel, Dutch lets Micah, a ruthless opportunist, worm his way into his side. Micah’s influence further alienates Dutch from the more rational gang members, hastening the gang’s demise.

Most startups have someone like Hosea in the team, who usually serve the role of Chief Operating Officer. When the founder recklessly pushes towards the vision, the COO turns that vague dream into executable plans and puts the team to the tasks. I have once experienced the departure of a COO, which seriously disrupted and demoralized the entire team. Without someone to meticulously organize the operations, the company degenerated into a chaotic arena where every team member acted on their own, many of them eventually leaving. Fortunately, the company could hire a new COO who then reined the chaos in. But the damage was done. Still, that was a better outcome than the fate of Dutch’s gang.

Arthur - lead enforcer / veteran individual contributor

Practically an adopted son of Dutch and Hosea, Arthur has been with the gang for more than two decades since he was picked up by them as a teenager. He is the lead enforcer of the gang, and an expert in all aspects of outlaw life from scouting, planning, gunfighting, escape, outdoor skills, explosives, horseback riding, and more. Whenever there’s a difficult or dangerous work to do, it is him who the gang calls for.

Dutch was his father and the gang his family. Arthur tries to stay loyal to both, but it quickly becomes impossible to be do so as Dutch starts to abandon his principles, then even the gang members, in the name of survival. On top of that, Arthur discovers that he has contracted tuberculosis, which was a terminal disease at the time. Everything he had held dear, along with his own life, was coming to an end. He makes peace with his inner demons, and continues to protect the gang members as much as possible. He dies helping gang members escape, staying loyal to the end.

Many startups have early team members who have been through thick and thin of the journey. They believe in the vision of founders and try their best to make it happen. They are respected by other team members as veterans and mentors who work and toil together. Unfortunately, there comes a moment when their opinion irreconcilably diverges from that of founders. Sometimes, their departure is a bittersweet yet amicable graduation. Other times, it’s a bitter expulsion. Regardless of how it goes, their departure marks an end of era for the company.

Other characters - zealots, opportunists, skeptics, survivors

All other members of the gang react to its downfall in different ways. John becomes completely disillusioned with Dutch and opposes him, openly arguing with Dutch and leaving the gang. On the other hand, Javier desperately clings to his memory of the gang in its heyday. He blindly follows Dutch to the end, turning a blind eye to his own growing doubts. Micah continues on his opportunistic attempts to win Dutch over, finally worming his way into Dutch. He is clearly after only one thing: the gang’s hidden stash of money. But most surviving members, like Pearson and Maribeth, quietly observe and stay with the gang and do their job until they can no longer bear the stress. Then they abandon the ship and disappear into the night.

Most startups fail, so it’s easy to observe how each member reacts to difficulties. I’ve seen my share of opportunists, who swear on their loyalty to the company but jump the ship at the first opportunity. There are also cultists of the founder, who drive away any unbeliever and accelerate the downfall of the company. Fortunately, such people are not the majority. During my years in the startup scene I’ve learned that, to my pleasant surprise, most are honest, hardworking people who try their best to save the company until they can no longer do so.


While it’s amusing to draw parallels between a 19th-century outlaw gang and a 21st-century startup, the similarities can only extend so far. As startup members, our failures don’t result in being hanged or shot. We operate within the law, albeit occasionally in gray areas or tax havens. Nevertheless, reflecting on how these characters might have fit into modern day startups was entertaining, a testament to their compelling portrayal in Red Dead Redemption 2. If you haven’t yet had the chance to play the game, I highly recommend it. You won’t be disappointed.