“I Have A Bad Feeling About This…”

Yoda and Obi-Wan Kenobi offer lessons for corporate innovators & startup CEOs

Scott Lenet
Risky Business
6 min readMay 26, 2022


Image: Aimee Blase

“In a dark place we find ourselves, and a little more knowledge lights our way.” — Jedi Grand Master Yoda

As leader of the Jedi council in Star Wars, Yoda was essentially their CEO. It was his job to see the future, a talent specifically honed by the visionary warrior monks, and yet he consistently allowed his vision to be “clouded by the dark side.” Yoda was funny, kind, beloved, and a caring teacher, but none of that stopped the fall of his entire governmental system. Despite his power, experience, authority, and wisdom, Yoda was shockingly bad at understanding what was happening around him until it was too late.

Over a period of a decade, the Jedi Grand Master worked directly with the Dark Lord of the Sith, Darth Sidious, who was hiding right under Yoda’s nose as the Supreme Chancellor of the Galactic Republic. Yoda’s failure to recognize changes as they were happening resulted in the rise of Palpatine’s empire and the overhaul of an entire culture’s way of life.

When faced with confusing facts and suspicious clues, what did Yoda do? He retreated to his chambers to meditate, but he did not take action.

Yes, Yoda got Kodaked.

Unfortunately this is all too common among the leadership of incumbent corporations. Many executives act as though they believe good times will never end, or as if they don’t care if it does.

Whether the example is the CEO of Kodak dismissing digital photography or the CEO of Blockbuster infamously downplaying the threat of Netflix, it seems there is always another market leader blissfully ignoring the winds of change.

In contrast to Yoda, Jedi Knight Obi-Wan Kenobi combined insight and action to preserve hope for the future during the Clone Wars and after the rise of Palpatine’s First Galactic Empire.

Seeing the future is also the goal of startup founders, corporate leaders, and venture capitalists. With that in mind, here are five lessons from the heroic actions of Obi-Wan Kenobi, and how corporate and startup executives alike can apply these learnings to devise transformational strategies and tactics:

1. Lookout for trouble by gathering “street level data”

When the Sith criticize the Jedi for arrogance, their argument is justified because the Jedi’s leader Yoda is out of touch. The Jedi Council sits in a literal ivory tower, sending Obi-Wan Kenobi on missions. As one of the Jedi’s top field agents, he is able to gather first-hand information to help understand what’s happening across the republic. It is Kenobi who first learns that Darth Tyrannus is actually Count Dooku during the Clone Wars, and he continues to pull on the threads of each clue he finds, always in a quest to learn more. Similarly, it is Kenobi who travels to Kamino in Episode II to unravel the mystery of the clone army.

The lesson for innovators is that you can’t meditate your way to organizational change. The Star Wars refrain, “I have a bad feeling about this,” might equate to Intel co-founder Andy Grove’s Only the Paranoid Survive. Grove’s definition of paranoia can be interpreted to mean that it’s important to pay attention at all times. This implies being unsatisfied with lack of clarity and investigating to acquire “street level” information about markets, customers, and the state of everyone else’s capabilities.

At a practical level, street level data means that corporations should meet lots of potentially disruptive startups, and startups should meet with potentially complementary or competitive corporations. Each should meet with as many customers and prospective customers as possible.

2. Be bold & decisive

Obi-Wan tracks down General Grievous on Utupau in Episode III. While the Separatist cyborg leader has killed dozens of Jedi, the vastly outnumbered Kenobi realizes he must take the risk of confronting Grievous. He leaps from above in the midst of dozens of enemy droids, delivering a line that has become meme fodder, “Hello, there.”

His opponent even declares, “General Kenobi. You are a bold one.”

Kenobi’s quick decision making also allows him to survive Order 66, when Commander Cody and his clone troopers turn on the Jedi.

Being bold means that innovators cannot afford to get stuck in analysis-paralysis. Once your organization has gathered information from the field, that information must be used to make decisions. That requires “pulling the trigger” by committing to new products, investments, commercial partnerships, and acquisitions.

3. Adapt your methods

In his ultimate showdown on Utupau with General Greivous, Kenobi uses a blaster to defeat the Separatist leader. The blaster is considered an inelegant tool for a Jedi. But Kenobi adapts to his circumstances to survive and win when his weapon of choice — the lightsaber — is unavailable.

Similarly, corporate and startup executives must look outside themselves and their organizations when innovation is required, as not everything can be accomplished internally. While internal product development and M&A may be the methods of comfort because these approaches offer full control, partnering (business development) and investing (corporate venture capital) can be powerful tools for harnessing external innovation. While these partial control options may be considered unsavory and unfamiliar, especially for corporations, they are powerful tools for innovation.

4. Don’t put all your eggs in one basket

When Padmé Amidala dies in childbirth as Anakin becomes Darth Vader, it is Kenobi who rescues Luke and Leia by devising a plan to “diversify” the Skywalker twins and preserve hope for the future. He personally brings Luke to Tatooine and entrusts Bail Organa, whom he knows to be a man of integrity and responsibility, to raise Leia as his daughter on Alderaan.

For startups and corporations, diversifying can take multiple forms. First and foremost, it implies not relying too heavily on any one buyer or supplier, per Michael Porter’s theory of competitive advantage. But for corporations seeking external innovation, diversifying also means taking a portfolio approach of multiple investments and startup commercial engagements. Given that a single M&A transaction requires approximately 10x the capital of a single venture capital investment according to Pitchbook, a portfolio approach may make financial sense, too.

5. Actively nurture the seeds of your future

Instead of slinking off to Dagoba to wallow in the swamp while growing ever more eccentric, Kenobi took on the personal responsibility of watching over Luke on Tatooine. Each seedling of hope received a watchful, safeguarding eye. At the moment of truth in Episode IV, when Luke needs Obi-Wan’s help, Kenobi is there.

In a startup or corporate environment, a good leader will do the same by standing up for innovation initiatives, to protect them from political enemies whose selfishness or short-sighted nature might sabotage the chance to create fresh opportunities for the corporation. Long term initiatives like new products and venture capital investments require diligent and active oversight and protection. Nurturing these efforts actively means appointing and empowering champions who will guard the success of these efforts.

I have a bad feeling about this” is one of the best running jokes of the Star Wars franchise. Nearly every major character utters the line at one point or another. These are also words to live by for corporate and startup leaders, because they are an emblem of awareness and proactivity.

This article was originally published on TechCrunch.

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Scott Lenet is President of Touchdown Ventures, a Registered Investment Adviser that provides “Venture Capital as a Service” to help corporations launch and manage their investment programs.

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Scott Lenet
Risky Business

Founder of Touchdown Ventures & DFJ Frontier, USC & UCLA adjunct professor, father of twins, Philly sports Phan, Forbes & TechCrunch contributor